Literature DB >> 12027685

Stereoselective synthesis of anti-alpha-(difluoromethyl)-beta-amino alcohols by boronic acid based three-component condensation. Stereoselective preparation of (2S,3R)-difluorothreonine.

G K Surya Prakash1, Mihirbaran Mandal, Stefan Schweizer, Nicos A Petasis, George A Olah.   

Abstract

Starting from optically active 3,3-difluorolactaldehyde, an alkenyl or aryl boronic acid, and an amine, a one-step three-component methodology was developed for the stereoselective preparation of anti-alpha-(difluoromethyl)-beta-amino alcohols. beta-Furyl-substituted anti-alpha-(difluoromethyl)-beta-amino alcohol was further elaborated to form (2S,3R)-difluorothreonine in high yield and ee.

Entities:  

Mesh：

Substances：

Year:  2002        PMID： 12027685     DOI： 10.1021/jo011116w

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


  4 in total

1.  Catalytic diastereoselective petasis reactions.

Authors:  Giovanni Muncipinto; Philip N Moquist; Stuart L Schreiber; Scott E Schaus
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-12       Impact factor: 15.336

2.  Phosphinite- and phosphite-based Type I palladacycles as highly active catalysts for addition reactions of arylboronic acids with aldehydes, α,β-unsaturated ketones, α-ketoesters, and aldimines.

Authors:  Ping He; Yong Lu; Qiao-Sheng Hu
Journal:  Tetrahedron Lett       Date:  2007-07-23       Impact factor: 2.415

3.  CF2H, a Hydrogen Bond Donor.

Authors:  Chanan D Sessler; Martin Rahm; Sabine Becker; Jacob M Goldberg; Fang Wang; Stephen J Lippard
Journal:  J Am Chem Soc       Date:  2017-06-27       Impact factor: 15.419

4.  Microwave-assisted nanocatalysis: A CuO NPs/rGO composite as an efficient and recyclable catalyst for the Petasis-borono-Mannich reaction.

Authors:  Anshu Dandia; Sarika Bansal; Ruchi Sharma; Kuldeep S Rathore; Vijay Parewa
Journal:  RSC Adv       Date:  2018-08-29       Impact factor: 3.361
  4 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.