One-Pot Synthesis of N-Substituted β-Amino Alcohols from Aldehydes and Isocyanides

A practical two‐stage one‐pot synthesis of N‐substituted β‐amino alcohols using aldehydes and isocyanides as starting materials has been developed. This method features mild reaction conditions, broad scope, and general tolerance of functional groups. Based on a less common central carbon–carbon bon...

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Veröffentlicht in:	Chemistry : a European journal Jg. 21; H. 21; S. 7808 - 7813
Hauptverfasser:	Cioc, Răzvan C., van der Niet, Daan J. H., Janssen, Elwin, Ruijter, Eelco, Orru, Romano V. A.
Format:	Journal Article
Sprache:	Englisch
Veröffentlicht:	Weinheim WILEY-VCH Verlag 18.05.2015 WILEY‐VCH Verlag Wiley
Schlagworte:	Albuterol - chemical synthesis Albuterol - chemistry Alcohols Aldehydes Aldehydes - chemical synthesis Aldehydes - chemistry amino alcohols Amino Alcohols - chemical synthesis Amino Alcohols - chemistry Asymmetry Bronchodilator Agents - chemical synthesis Bronchodilator Agents - chemistry Chemistry Chemistry, Multidisciplinary Combinatorial Chemistry Techniques Cyanides - chemical synthesis Cyanides - chemistry Drugs isocyanide Lewis base Lewis bases Physical Sciences salbutamol Science & Technology Synthesis Tolerances Upgrading INSERTION salbutamol amino alcohols Lewis bases DISCOVERY isocyanide MULTICOMPONENT REACTIONS aldehydes ALPHA-ADDITIONS CHEMISTRY AGENTS PASSERINI-TYPE REACTIONS INHIBITORS DERIVATIVES AGONIST
ISSN:	0947-6539, 1521-3765, 1521-3765
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Abstract	A practical two‐stage one‐pot synthesis of N‐substituted β‐amino alcohols using aldehydes and isocyanides as starting materials has been developed. This method features mild reaction conditions, broad scope, and general tolerance of functional groups. Based on a less common central carbon–carbon bond disconnection, this protocol complements traditional approaches that involve amines and various carbon electrophiles (epoxides, α‐halo ketones, β‐halohydrins). Medicinally relevant products can be prepared in a concise and efficient way from simple building blocks, as demonstrated in the synthesis of the antiasthma drug salbutamol. Upgrading the synthesis to an enantioselective variant is also feasible. Retrosynthesis revisited: A practical and general two‐stage one‐pot synthesis of N‐substituted β‐amino alcohols using aldehydes and isocyanides as starting inputs is described (see scheme). Medicinally relevant compounds can be prepared in a concise and efficient way from simple building blocks, as demonstrated by the synthesis of the antiasthmatic drug salbutamol. The reaction can readily be made asymmetric by using a chiral Lewis base catalyst.
AbstractList	A practical two-stage one-pot synthesis of N-substituted β-amino alcohols using aldehydes and isocyanides as starting materials has been developed. This method features mild reaction conditions, broad scope, and general tolerance of functional groups. Based on a less common central carbon-carbon bond disconnection, this protocol complements traditional approaches that involve amines and various carbon electrophiles (epoxides, α-halo ketones, β-halohydrins). Medicinally relevant products can be prepared in a concise and efficient way from simple building blocks, as demonstrated in the synthesis of the antiasthma drug salbutamol. Upgrading the synthesis to an enantioselective variant is also feasible. A practical two‐stage one‐pot synthesis of N‐substituted β‐amino alcohols using aldehydes and isocyanides as starting materials has been developed. This method features mild reaction conditions, broad scope, and general tolerance of functional groups. Based on a less common central carbon–carbon bond disconnection, this protocol complements traditional approaches that involve amines and various carbon electrophiles (epoxides, α‐halo ketones, β‐halohydrins). Medicinally relevant products can be prepared in a concise and efficient way from simple building blocks, as demonstrated in the synthesis of the antiasthma drug salbutamol. Upgrading the synthesis to an enantioselective variant is also feasible. Retrosynthesis revisited: A practical and general two‐stage one‐pot synthesis of N‐substituted β‐amino alcohols using aldehydes and isocyanides as starting inputs is described (see scheme). Medicinally relevant compounds can be prepared in a concise and efficient way from simple building blocks, as demonstrated by the synthesis of the antiasthmatic drug salbutamol. The reaction can readily be made asymmetric by using a chiral Lewis base catalyst. A practical two-stage one-pot synthesis of N-substituted -amino alcohols using aldehydes and isocyanides as starting materials has been developed. This method features mild reaction conditions, broad scope, and general tolerance of functional groups. Based on a less common central carbon-carbon bond disconnection, this protocol complements traditional approaches that involve amines and various carbon electrophiles (epoxides, -halo ketones, -halohydrins). Medicinally relevant products can be prepared in a concise and efficient way from simple building blocks, as demonstrated in the synthesis of the antiasthma drug salbutamol. Upgrading the synthesis to an enantioselective variant is also feasible. A practical two-stage one-pot synthesis of N-substituted β-amino alcohols using aldehydes and isocyanides as starting materials has been developed. This method features mild reaction conditions, broad scope, and general tolerance of functional groups. Based on a less common central carbon-carbon bond disconnection, this protocol complements traditional approaches that involve amines and various carbon electrophiles (epoxides, α-halo ketones, β-halohydrins). Medicinally relevant products can be prepared in a concise and efficient way from simple building blocks, as demonstrated in the synthesis of the antiasthma drug salbutamol. Upgrading the synthesis to an enantioselective variant is also feasible.A practical two-stage one-pot synthesis of N-substituted β-amino alcohols using aldehydes and isocyanides as starting materials has been developed. This method features mild reaction conditions, broad scope, and general tolerance of functional groups. Based on a less common central carbon-carbon bond disconnection, this protocol complements traditional approaches that involve amines and various carbon electrophiles (epoxides, α-halo ketones, β-halohydrins). Medicinally relevant products can be prepared in a concise and efficient way from simple building blocks, as demonstrated in the synthesis of the antiasthma drug salbutamol. Upgrading the synthesis to an enantioselective variant is also feasible. A practical two-stage one-pot synthesis of N-substituted beta -amino alcohols using aldehydes and isocyanides as starting materials has been developed. This method features mild reaction conditions, broad scope, and general tolerance of functional groups. Based on a less common central carbon-carbon bond disconnection, this protocol complements traditional approaches that involve amines and various carbon electrophiles (epoxides, alpha -halo ketones, beta -halohydrins). Medicinally relevant products can be prepared in a concise and efficient way from simple building blocks, as demonstrated in the synthesis of the antiasthma drug salbutamol. Upgrading the synthesis to an enantioselective variant is also feasible. Retrosynthesis revisited: A practical and general two-stage one-pot synthesis of N-substituted beta -amino alcohols using aldehydes and isocyanides as starting inputs is described (see scheme). Medicinally relevant compounds can be prepared in a concise and efficient way from simple building blocks, as demonstrated by the synthesis of the antiasthmatic drug salbutamol. The reaction can readily be made asymmetric by using a chiral Lewis base catalyst.
Author	Orru, Romano V. A. Ruijter, Eelco Cioc, Răzvan C. van der Niet, Daan J. H. Janssen, Elwin
Author_xml	– sequence: 1 givenname: Răzvan C. surname: Cioc fullname: Cioc, Răzvan C. organization: Department of Chemistry & Pharmaceutical Sciences and Amsterdam Institute for Molecules Medicines and Systems (AIMMS), VU University Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam (The Netherlands) – sequence: 2 givenname: Daan J. H. surname: van der Niet fullname: van der Niet, Daan J. H. organization: Department of Chemistry & Pharmaceutical Sciences and Amsterdam Institute for Molecules Medicines and Systems (AIMMS), VU University Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam (The Netherlands) – sequence: 3 givenname: Elwin surname: Janssen fullname: Janssen, Elwin organization: Department of Chemistry & Pharmaceutical Sciences and Amsterdam Institute for Molecules Medicines and Systems (AIMMS), VU University Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam (The Netherlands) – sequence: 4 givenname: Eelco surname: Ruijter fullname: Ruijter, Eelco organization: Department of Chemistry & Pharmaceutical Sciences and Amsterdam Institute for Molecules Medicines and Systems (AIMMS), VU University Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam (The Netherlands) – sequence: 5 givenname: Romano V. A. surname: Orru fullname: Orru, Romano V. A. email: r.v.a.orru@vu.nl organization: Department of Chemistry & Pharmaceutical Sciences and Amsterdam Institute for Molecules Medicines and Systems (AIMMS), VU University Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam (The Netherlands)
BackLink	https://www.ncbi.nlm.nih.gov/pubmed/25868115$$D View this record in MEDLINE/PubMed
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Keywords	INSERTION salbutamol amino alcohols Lewis bases DISCOVERY isocyanide MULTICOMPONENT REACTIONS aldehydes ALPHA-ADDITIONS CHEMISTRY AGENTS PASSERINI-TYPE REACTIONS INHIBITORS DERIVATIVES AGONIST
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Snippet	A practical two‐stage one‐pot synthesis of N‐substituted β‐amino alcohols using aldehydes and isocyanides as starting materials has been developed. This method... A practical two-stage one-pot synthesis of N-substituted -amino alcohols using aldehydes and isocyanides as starting materials has been developed. This method... A practical two-stage one-pot synthesis of N-substituted β-amino alcohols using aldehydes and isocyanides as starting materials has been developed. This method... A practical two-stage one-pot synthesis of N-substituted beta -amino alcohols using aldehydes and isocyanides as starting materials has been developed. This...
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SubjectTerms	Albuterol - chemical synthesis Albuterol - chemistry Alcohols Aldehydes Aldehydes - chemical synthesis Aldehydes - chemistry amino alcohols Amino Alcohols - chemical synthesis Amino Alcohols - chemistry Asymmetry Bronchodilator Agents - chemical synthesis Bronchodilator Agents - chemistry Chemistry Chemistry, Multidisciplinary Combinatorial Chemistry Techniques Cyanides - chemical synthesis Cyanides - chemistry Drugs isocyanide Lewis base Lewis bases Physical Sciences salbutamol Science & Technology Synthesis Tolerances Upgrading
Title	One-Pot Synthesis of N-Substituted β-Amino Alcohols from Aldehydes and Isocyanides
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