Literature DB >> 16930068

Concise synthesis of enantiopure alpha-trifluoromethyl alanines, diamines, and amino alcohols via the Strecker-type reaction.

Florent Huguenot1, Thierry Brigaud.   

Abstract

Diastereomerically pure alpha-trifluoromethyl alpha-amino nitriles obtained by Strecker-type reactions from chiral CF3 imines and iminium proved to be very attractive versatile intermediates for the synthesis of various alpha-trifluoromethyl amino compounds. From these synthons, both enantiomers of alpha-trifluoromethyl alanine, trifluoromethyl 1,2-diamines, and amino alcohols were conveniently obtained in enantiopure form in high yields in a few steps.

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Year:  2006        PMID: 16930068     DOI: 10.1021/jo0607717

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  3 in total

1.  Strategies for the Catalytic Enantioselective Synthesis of α-Trifluoromethyl Amines.

Authors:  Chibueze I Onyeagusi; Steven J Malcolmson
Journal:  ACS Catal       Date:  2020-10-12       Impact factor: 13.084

2.  Efficient three-component Strecker reaction of aldehydes/ketones via NHC-amidate palladium(II) complex catalysis.

Authors:  Jamie Jarusiewicz; Yvonne Choe; Kyung Soo Yoo; Chan Pil Park; Kyung Woon Jung
Journal:  J Org Chem       Date:  2009-04-03       Impact factor: 4.354

Review 3.  CF3-substituted carbocations: underexploited intermediates with great potential in modern synthetic chemistry.

Authors:  Anthony J Fernandes; Armen Panossian; Bastien Michelet; Agnès Martin-Mingot; Frédéric R Leroux; Sébastien Thibaudeau
Journal:  Beilstein J Org Chem       Date:  2021-02-03       Impact factor: 2.883

  3 in total

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