Regio- and diastereoselective Reformatsky reaction of chiral fluoroalkyl α,β-unsaturated N-tert-butanesulfinyl ketimines: Efficient asymmetric synthesis of β-fluoroalkyl β-vinyl β-amino esters

Highly regio- and diastereoselective Reformatsky reaction of stable, chiral fluoroalkyl α,β-unsaturated N-tert-butanesulfinyl ketimines was developed, which provided an efficient method for the asymmetric synthesis of structurally diverse β-tetrasubstituted β-fluoroalkyl β-vinyl β-amino esters in go...

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Published inTetrahedron Vol. 74; no. 24; pp. 3074 - 3080
Main Authors Peng, Ying-Ying, Liu, Peng, Liu, Zhen-Jiang, Liu, Jin-Tao, Mao, Hai-Fang, Yao, Yue-Liang
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 14.06.2018
Elsevier
Subjects
Chemistry
Chemistry, Organic
Fluoroalkyl
N-tert-butanesulfinyl ketimines
Physical Sciences
Reformatsky reaction
Science & Technology
β-amino esters
N-tert-butanesulfinyl ketimines
Fluoroalkyl
Reformatsky reaction
β-amino esters
ALCOHOLS
ACID
IMINES
BIOLOGICAL-ACTIVITY
beta-amino esters
CONVENIENT
LITHIUM (ALPHA-METHYLBENZYL)ALLYLAMIDE
ADDA
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Summary:Highly regio- and diastereoselective Reformatsky reaction of stable, chiral fluoroalkyl α,β-unsaturated N-tert-butanesulfinyl ketimines was developed, which provided an efficient method for the asymmetric synthesis of structurally diverse β-tetrasubstituted β-fluoroalkyl β-vinyl β-amino esters in good yields and with excellent diastereoselectivities (dr up to 96:4). [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2018.05.014