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Enantioselective Synthesis of Homoallylamines by Nucleophilic Addition of Chirally Modified Allylboron Reagents to Imines
Author(s) -
Itsuno Shinichi,
Watanabe Katsuhiro,
Ito Koichi,
ElShehawy Ashraf A.,
Sarhan Ali A.
Publication year - 1997
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199701091
Subject(s) - enantioselective synthesis , reagent , nucleophile , chemistry , tosyl , combinatorial chemistry , ligand (biochemistry) , organic chemistry , nucleophilic addition , catalysis , receptor , biochemistry
N‐silylated imines are well‐suited for reaction with chirally modified allylboron reagents to give enantiomerically enriched primary homoallylamines in high yields [Eq. (a)]. The chiral ligand, here N ‐tosyl‐(–)‐norephedrin, can be recovered after the reaction and used again to generate the chiral allylboron reagent. Ts = p ‐toluenesulfonyl.