New Family of Cyclopropanating Reagents: Synthesis, Reactivity, and Stability Studies of Iodomethylzinc Phenoxides
Eine wertvolle Alternative zum herkömmlichen Simmons‐Smith‐Reagens sind die Titelverbindungen (siehe Schema), die einfach in der Herstellung und sehr reaktiv gegenüber nichtfunktionalisierten Olefinen sind.
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| Published in: | Angewandte Chemie Vol. 112; no. 24; pp. 4713 - 4716 |
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| Main Authors: | , , , |
| Format: | Journal Article |
| Language: | English |
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Weinheim
WILEY-VCH Verlag GmbH
15.12.2000
WILEY‐VCH Verlag GmbH |
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| ISSN: | 0044-8249, 1521-3757 |
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| Abstract | Eine wertvolle Alternative zum herkömmlichen Simmons‐Smith‐Reagens sind die Titelverbindungen (siehe Schema), die einfach in der Herstellung und sehr reaktiv gegenüber nichtfunktionalisierten Olefinen sind. |
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| AbstractList | Eine wertvolle Alternative zum herkömmlichen Simmons‐Smith‐Reagens sind die Titelverbindungen (siehe Schema), die einfach in der Herstellung und sehr reaktiv gegenüber nichtfunktionalisierten Olefinen sind. |
| Author | Charette, André B. Wilb, Nicole Francoeur, Sébastien Martel, Jonathan |
| Author_xml | – sequence: 1 givenname: André B. surname: Charette fullname: Charette, André B. email: andre.charette@umontreal.ca organization: Département de Chimie Université de Montréal P.O. Box 6128, Station Downtown, Montréal (Canada) Fax: (+1) 514-343-5900 – sequence: 2 givenname: Sébastien surname: Francoeur fullname: Francoeur, Sébastien organization: Département de Chimie Université de Montréal P.O. Box 6128, Station Downtown, Montréal (Canada) Fax: (+1) 514-343-5900 – sequence: 3 givenname: Jonathan surname: Martel fullname: Martel, Jonathan organization: Département de Chimie Université de Montréal P.O. Box 6128, Station Downtown, Montréal (Canada) Fax: (+1) 514-343-5900 – sequence: 4 givenname: Nicole surname: Wilb fullname: Wilb, Nicole organization: Département de Chimie Université de Montréal P.O. Box 6128, Station Downtown, Montréal (Canada) Fax: (+1) 514-343-5900 |
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| Cites_doi | 10.1039/co9940100219 10.1016/S0040-4039(00)73718-X 10.1002/(SICI)1521-3757(19990816)111:16<2533::AID-ANGE2533>3.0.CO;2-I 10.1055/s-1994-23046 10.1021/ja01552a080 10.1016/0040-4020(68)89007-6 10.1016/S0040-4039(98)01954-6 10.1021/jo00025a007 10.1016/S0040-4039(01)93745-1 10.1021/ja9621004 10.1021/ol990660c 10.1021/ja01525a036 10.1093/oso/9780198501213.003.0013 10.1021/ja00150a046 10.1246/bcsj.70.207 10.1016/S0040-4039(01)82791-X 10.1016/S0040-4039(00)73511-8 10.2174/0929867302666220216234752 |
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| Copyright | 2000 WILEY‐VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany |
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| Notes | ArticleID:ANGE4713 ark:/67375/WNG-MCN72L53-D istex:5F5CE3D54F30E61355D2319773493B2E9629490D This work was supported by the E.W.R. Steacie Fund, the National Science and Engineering Research Council (NSERC) of Canada, Merck Frosst Canada, Boehringer Ingelheim (Canada), F.C.A.R. (Québec), and the Université de Montréal. J.M. and S.F. are grateful to NSERC and F.C.A.R. respectively for postgraduate fellowships. |
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| References | For recent examples, see: callipeltoside A: A. Zampella , M. V. D'Auria , L. Minale , C. Debitus , C. Roussakis , J. Am. Chem. Soc. 1996, 118, 11 085-11 088; bisgersolanolide A. D. Rodríguez , J.-G. Shi , Org. Lett. 1999, 1, 337-340; quinoxapeptins A-C H. E. Simmons , R. D. Smith , J. Am. Chem. Soc. 1958, 80, 5323-5324 J. B. Rodriguez , V. E. Marquez , M. C. Nicklaus , J. J. Barchi, Jr. , Tetrahedron Lett. 1993, 34, 6233-6236. J. Salaün , Curr. Med. Chem. 1995, 2, 511-542. The Chemistry of the Cyclopropyl Group (Ed.: Z. Rappoport), Wiley, Chichester, 1987 Small Ring Compounds in Organic Synthesis VI, Vol. 207 (Ed.: A. de Meijere), Springer, Berlin, 2000, and references therein A. B. Charette in Organozinc Reagents. A Practical Approach (Eds.: P. Knochel, P. Jones), Oxford University, Oxford, 1999, pp. 263-283 J. Salaün in Small Ring Compounds in Organic Synthesis VI, Vol. 207 (Ed.: A. de Meijere), Springer, Berlin, 2000, pp. 1-67 Methoden Org. Chem. (Houben-Weyl) 4th ed. 1952-, Vol. E17/a,b. F. Cluet , A. Haudrechy , P. Le Ber , P. Sinaÿ , Synlett 1994, 913-915 D. L. Boger , M. W. Ledeboer , M. Kume , Q. Jin , Angew. Chem. 1999, 111, 2533-2536; Angew. Chem. Int. Ed. 1999, 38, 2424-2426. J. Furukawa , N. Kawabata , J. Nishimura , Tetrahedron Lett. 1966, 3353-3354 For a review, see: H. E. Simmons , T. L. Cairns , S. A. Vladuchick , C. M. Hoiness , Org. React. 1973, 20, 1-131 S. E. Denmark , J. P. Edwards , J. Org. Chem. 1991, 56, 6974-6981. J. Furukawa , N. Kawabata , J. Nishimura , Tetrahedron 1968, 24, 53-58. W. B. Motherwell , C. J. Nutley , Contemp. Org. Synth. 1994, 1, 219-241. Z. Q. Yang , J. C. Lorenz , Y. Shi , Tetrahedron Lett. 1998, 39, 8621-8624. A. B. Charette , C. Brochu , J. Am. Chem. Soc. 1995, 117, 11 367-11 368. Katsuki and co-workers have recently reported the use of a 3,3′-disubstituted binaphthol to perform the enantioselective cyclopropanation of allylic alcohols but six equivalents of Et2Zn were used per equivalent of phenol (threefold excess). Free EtZnCH2I is presumably formed in this system (and not ArOZnCH2I): H. Kitajima , K. Ito , Y. Aoki , T. Katsuki , Bull. Chem. Soc. Jpn. 1997, 70, 207-217. H. E. Simmons , R. D. Smith , J. Am. Chem. Soc. 1959, 81, 4256-4264. Methods Org. Chem. (Houben-Weyl) 4th ed. 1952-, Vol. E17/c. Y. Zhao , T.-F. Yang , M. Lee , B. K. Chun , J. Du , R. F. Schinazi , D. Lee , M. G. Newton , C. K. Chu , Tetrahedron Lett. 1994, 35, 5405-5408 E. K. Lehnert , J. S. Sawyer , T. L. Macdonald , Tetrahedron Lett. 1989, 30, 5215-5218. 1989; 30 1993; 34 1968; 24 1998; 39 1996 1999 1999; 118 1 111 1959; 81 1973; 20 1997; 70 1991; 56 2000 1987 1995; 117 1994; 35 1994 1958; 80 1995; 2 1994; 1 1999 1966 (10.1002/1521-3757(20001215)112:24<4713::AID-ANGE4713>3.0.CO;2-A-BIB4A) 1987 Salaün (10.1002/1521-3757(20001215)112:24<4713::AID-ANGE4713>3.0.CO;2-A-BIB3B) 1995; 2 10.1002/1521-3757(20001215)112:24<4713::AID-ANGE4713>3.0.CO;2-A-BIB5 Denmark (10.1002/1521-3757(20001215)112:24<4713::AID-ANGE4713>3.0.CO;2-A-BIB9) 1991; 56 10.1002/1521-3757(20001215)112:24<4713::AID-ANGE4713>3.0.CO;2-A-BIB4 Charette (10.1002/1521-3757(20001215)112:24<4713::AID-ANGE4713>3.0.CO;2-A-BIB6A) 1999 Motherwell (10.1002/1521-3757(20001215)112:24<4713::AID-ANGE4713>3.0.CO;2-A-BIB7B) 1994; 1 Yang (10.1002/1521-3757(20001215)112:24<4713::AID-ANGE4713>3.0.CO;2-A-BIB11) 1998; 39 10.1002/1521-3757(20001215)112:24<4713::AID-ANGE4713>3.0.CO;2-A-BIB8 10.1002/1521-3757(20001215)112:24<4713::AID-ANGE4713>3.0.CO;2-A-BIB7 10.1002/1521-3757(20001215)112:24<4713::AID-ANGE4713>3.0.CO;2-A-BIB4C Charette (10.1002/1521-3757(20001215)112:24<4713::AID-ANGE4713>3.0.CO;2-A-BIB10) 1995; 117 Salaün (10.1002/1521-3757(20001215)112:24<4713::AID-ANGE4713>3.0.CO;2-A-BIB3A) 2000 Kitajima (10.1002/1521-3757(20001215)112:24<4713::AID-ANGE4713>3.0.CO;2-A-BIB15) 1997; 70 Cluet (10.1002/1521-3757(20001215)112:24<4713::AID-ANGE4713>3.0.CO;2-A-BIB2B) 1994 Furukawa (10.1002/1521-3757(20001215)112:24<4713::AID-ANGE4713>3.0.CO;2-A-BIB8A) 1966 Furukawa (10.1002/1521-3757(20001215)112:24<4713::AID-ANGE4713>3.0.CO;2-A-BIB8B) 1968; 24 Rodriguez (10.1002/1521-3757(20001215)112:24<4713::AID-ANGE4713>3.0.CO;2-A-BIB2C) 1993; 34 (10.1002/1521-3757(20001215)112:24<4713::AID-ANGE4713>3.0.CO;2-A-BIB4B) 2000 Lehnert (10.1002/1521-3757(20001215)112:24<4713::AID-ANGE4713>3.0.CO;2-A-BIB13) 1989; 30 Simmons (10.1002/1521-3757(20001215)112:24<4713::AID-ANGE4713>3.0.CO;2-A-BIB5A) 1958; 80 10.1002/1521-3757(20001215)112:24<4713::AID-ANGE4713>3.0.CO;2-A-BIB6B Rodríguez (10.1002/1521-3757(20001215)112:24<4713::AID-ANGE4713>3.0.CO;2-A-BIB1.2) 1999; 1 Simmons (10.1002/1521-3757(20001215)112:24<4713::AID-ANGE4713>3.0.CO;2-A-BIB7A) 1973; 20 10.1002/1521-3757(20001215)112:24<4713::AID-ANGE4713>3.0.CO;2-A-BIB2 Zhao (10.1002/1521-3757(20001215)112:24<4713::AID-ANGE4713>3.0.CO;2-A-BIB2A) 1994; 35 Boger (10.1002/1521-3757(20001215)112:24<4713::AID-ANGE4713>3.0.CO;2-A-BIB1.3) 1999; 11138 Simmons (10.1002/1521-3757(20001215)112:24<4713::AID-ANGE4713>3.0.CO;2-A-BIB5B) 1959; 81 Zampella (10.1002/1521-3757(20001215)112:24<4713::AID-ANGE4713>3.0.CO;2-A-BIB1.1) 1996; 118 |
| References_xml | – reference: Y. Zhao , T.-F. Yang , M. Lee , B. K. Chun , J. Du , R. F. Schinazi , D. Lee , M. G. Newton , C. K. Chu , Tetrahedron Lett. 1994, 35, 5405-5408; – reference: E. K. Lehnert , J. S. Sawyer , T. L. Macdonald , Tetrahedron Lett. 1989, 30, 5215-5218. – reference: W. B. Motherwell , C. J. Nutley , Contemp. Org. Synth. 1994, 1, 219-241. – reference: D. L. Boger , M. W. Ledeboer , M. Kume , Q. Jin , Angew. Chem. 1999, 111, 2533-2536; Angew. Chem. Int. Ed. 1999, 38, 2424-2426. – reference: Methoden Org. Chem. (Houben-Weyl) 4th ed. 1952-, Vol. E17/a,b. – reference: A. B. Charette , C. Brochu , J. Am. Chem. Soc. 1995, 117, 11 367-11 368. – reference: Methods Org. Chem. (Houben-Weyl) 4th ed. 1952-, Vol. E17/c. – reference: J. B. Rodriguez , V. E. Marquez , M. C. Nicklaus , J. J. Barchi, Jr. , Tetrahedron Lett. 1993, 34, 6233-6236. – reference: J. Salaün in Small Ring Compounds in Organic Synthesis VI, Vol. 207 (Ed.: A. de Meijere), Springer, Berlin, 2000, pp. 1-67; – reference: H. E. Simmons , R. D. Smith , J. Am. Chem. Soc. 1959, 81, 4256-4264. – reference: For a review, see: H. E. Simmons , T. L. Cairns , S. A. Vladuchick , C. M. Hoiness , Org. React. 1973, 20, 1-131; – reference: For recent examples, see: callipeltoside A: A. Zampella , M. V. D'Auria , L. Minale , C. Debitus , C. Roussakis , J. Am. Chem. Soc. 1996, 118, 11 085-11 088; bisgersolanolide: – reference: S. E. Denmark , J. P. Edwards , J. Org. Chem. 1991, 56, 6974-6981. – reference: Katsuki and co-workers have recently reported the use of a 3,3′-disubstituted binaphthol to perform the enantioselective cyclopropanation of allylic alcohols but six equivalents of Et2Zn were used per equivalent of phenol (threefold excess). Free EtZnCH2I is presumably formed in this system (and not ArOZnCH2I): H. Kitajima , K. Ito , Y. Aoki , T. Katsuki , Bull. Chem. Soc. Jpn. 1997, 70, 207-217. – reference: Z. Q. Yang , J. C. Lorenz , Y. Shi , Tetrahedron Lett. 1998, 39, 8621-8624. – reference: J. Furukawa , N. Kawabata , J. Nishimura , Tetrahedron Lett. 1966, 3353-3354; – reference: H. E. Simmons , R. D. Smith , J. Am. Chem. Soc. 1958, 80, 5323-5324; – reference: Small Ring Compounds in Organic Synthesis VI, Vol. 207 (Ed.: A. de Meijere), Springer, Berlin, 2000, and references therein; – reference: J. Salaün , Curr. Med. Chem. 1995, 2, 511-542. – reference: F. Cluet , A. Haudrechy , P. Le Ber , P. Sinaÿ , Synlett 1994, 913-915; – reference: J. Furukawa , N. Kawabata , J. Nishimura , Tetrahedron 1968, 24, 53-58. – reference: A. D. Rodríguez , J.-G. Shi , Org. Lett. 1999, 1, 337-340; quinoxapeptins A-C: – reference: The Chemistry of the Cyclopropyl Group (Ed.: Z. Rappoport), Wiley, Chichester, 1987; – reference: A. B. Charette in Organozinc Reagents. A Practical Approach (Eds.: P. Knochel, P. 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| Title | New Family of Cyclopropanating Reagents: Synthesis, Reactivity, and Stability Studies of Iodomethylzinc Phenoxides |
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