✦ LIBER ✦

Direct Asymmetric α-Sulfamidation of α-Branched Aldehydes: A Novel Approach to Enamine Catalysis

✍ Scribed by Henning Vogt; Thomas Baumann; Martin Nieger; Stefan Bräse

Publisher: John Wiley and Sons
Year: 2006
Tongue: English
Weight: 431 KB
Volume: 2006
Category: Article
ISSN: 1434-193X
DOI: 10.1002/ejoc.200600587

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

Proline‐catalysed reactions between α‐branched aldehydes and sulfonyl azides provide scalemic configurationally stabilised α‐sulfamidated products with ee values of up to 86 %. The reactions can also be carried out in a one‐pot fashion, with catalyst, aldehyde, sulfonyl chloride and sodium azide. The proposed mechanism differs fundamentally from the mechanistic model usually ascribed to enamine catalysis, containing as a key step the diastereoselective cycloaddition of the azide to an enamine formed in situ. The products obtained in the reaction can be converted into the corresponding unnatural amino acids in two additional steps.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

📜 SIMILAR VOLUMES

Direct Asymmetric α-Sulfamidation of α-B

Direct Asymmetric α-Sulfamidation of α-Branched Aldehydes: A Novel Approach to Enamine Catalysis.

✍ Henning Vogt; Thomas Baumann; Martin Nieger; Stefan Braese 📂 Article 📅 2007 🏛 John Wiley and Sons ⚖ 47 KB 👁 1 views

Direct Organo-Catalytic Asymmetric α-Ami

Direct Organo-Catalytic Asymmetric α-Amination of Aldehydes—A Simple Approach to Optically Active α-Amino Aldehydes, α-Amino Alcohols, and α-Amino Acids

✍ Anders Bøgevig; Karsten Juhl; Nagaswamy Kumaragurubaran; Wei Zhuang; Karl Anker 📂 Article 📅 2002 🏛 John Wiley and Sons 🌐 English ⚖ 99 KB 👁 1 views

Direct Organo-Catalytic Asymmetric α-Ami

Direct Organo-Catalytic Asymmetric α-Amination of Aldehydes—A Simple Approach to Optically Active α-Amino Aldehydes, α-Amino Alcohols, and α-Amino Acids

✍ Anders Bøgevig; Karsten Juhl; Nagaswamy Kumaragurubaran; Wei Zhuang; Karl Anker 📂 Article 📅 2002 🏛 John Wiley and Sons 🌐 English ⚖ 99 KB 👁 1 views

Direct Organo-Catalytic Asymmetric α-Ami

Direct Organo-Catalytic Asymmetric α-Amination of Aldehydes — A Simple Approach to Optically Active α-Amino Aldehydes, α-Amino Alcohols, and α-Amino Acids.

✍ Anders Boegevig; Karsten Juhl; Nagaswamy Kumaragurubaran; Wei Zhuang; Karl Anker 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 34 KB 👁 1 views

Enantioselective Linchpin Catalysis by S

Enantioselective Linchpin Catalysis by SOMO Catalysis: An Approach to the Asymmetric α-Chlorination of Aldehydes and Terminal Epoxide Formation

✍ Muriel Amatore; Teresa D. Beeson; Sean P. Brown; David W. C. MacMillan 📂 Article 📅 2009 🏛 John Wiley and Sons 🌐 English ⚖ 620 KB

## Abstract Dreh‐ und Angelpunkt: Erstmals wurde eine SOMO‐Aktivierung genutzt, um Aldehyde in α‐Stellung zu chlorieren. Diese Umwandlung lässt sich als Teil eines „Linchpin“‐Katalyseprozesses einsetzen, der die enantioselektive Synthese terminaler Epoxide ermöglicht (siehe Schema).magnified image

Enantioselective Linchpin Catalysis by S

Enantioselective Linchpin Catalysis by SOMO Catalysis: An Approach to the Asymmetric α-Chlorination of Aldehydes and Terminal Epoxide Formation

✍ Muriel Amatore; Teresa D. Beeson; Sean P. Brown; David W. C. MacMillan 📂 Article 📅 2009 🏛 John Wiley and Sons 🌐 English ⚖ 620 KB