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Highly Regio‐ and Diastereoselective Addition of Organolithium Reagents to Chiral Fluoroalkyl α,β‐Unsaturated N ‐ tert ‐Butanesulfinyl Ketimines: A General and Efficient Access to α‐Tertiary Fluoroalkyl Allylic Amines and α‐Fluoroalkyl α‐Amino Acids
Author(s) -
Liu Peng,
Liu ZhenJiang,
Wu Fanhong
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400992
Subject(s) - chemistry , reagent , allylic rearrangement , organic chemistry , carbon fibers , organolithium compounds , enantioselective synthesis , combinatorial chemistry , catalysis , ion , materials science , composite number , deprotonation , composite material
Highly regio‐ and diastereoselective 1,2‐addition of organolithium reagents to chiral fluoroalkyl α,β‐unsaturated N ‐ tert ‐butanesulfinyl ketimines was developed, providing a general and efficient method for the asymmetric synthesis of structurally diverse α‐tertiary fluoroalkyl allylic amines in high yields and with excellent diastereoselectivities (dr up to>99:1). The synthetic application of the method was demonstrated by the rapid and convenient preparation of challenging α‐fluoroalkyl α‐amino acids with α‐tetrasubstituted carbon.