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Highly Diastereoselective Indium‐Mediated Allenylation of N ‐ tert ‐Butanesulfinyl Imino Ester: Efficient Synthesis of Optically Active α‐Allenylglycines
Author(s) -
Jin ShenShuang,
Xu MingHua
Publication year - 2010
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.201000688
Subject(s) - chemistry , indium , halide , optically active , proline , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis , amino acid , biochemistry
An efficient and practical asymmetric synthesis of highly enantiomerically enriched α‐allenylglycines by room temperature indium‐mediated allenylation of chiral N‐tert ‐butanesulfinyl imino esters with propargylic halides is described. The synthetic utilities of the approach were demonstrated by the rapid and convenient preparation of challenging cis ‐substituted proline derivatives.