Literature DB >> 16839124

Fluorination-free synthesis of a 4,4-difluoro-3,3-dimethylproline derivative.

Lijian Chen1, Young Mi Kim, David J Kucera, Katheryn E Harrison, Sogole Bahmanyar, Jill M Scott, Daniel Yazbeck.   

Abstract

A Claisen rearrangement/iodolactamization sequence starting from commercially available trifluoroacetaldehyde methyl hemiacetal, followed by a classical chemical resolution, provided enantiomerically pure 4,4-difluoro-3,3-dimethylproline (S)-1. No hazardous fluorination reagents were used, and the overall yield over 12 steps was greater than 28%.

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Year:  2006        PMID: 16839124     DOI: 10.1021/jo060057p

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


  2 in total

1.  Synthesis of bioactive fluoropyrrolidines via copper(i)-catalysed asymmetric 1,3-dipolar cycloaddition of azomethine ylides.

Authors:  Xiao Xu; Longzhu Bao; Lu Ran; Zhenyan Yang; Dingce Yan; Chun-Jiang Wang; Huailong Teng
Journal:  Chem Sci       Date:  2021-12-07       Impact factor: 9.825

2.  Recent developments in the Reformatsky-Claisen rearrangement.

Authors:  Jun Ishihara; Susumi Hatakeyama
Journal:  Molecules       Date:  2012-11-30       Impact factor: 4.411

  2 in total

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