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Catalytic Asymmetric Mannich Reaction of Glycine Derivatives with N ‐Tosylimines using Copper(I)/TF‐BiphamPhos Complex
Author(s) -
Liang Gang,
Tong MinChao,
Tao Haiyan,
Wang ChunJiang
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.201000252
Subject(s) - chemistry , mannich reaction , glycine , catalysis , tetrafluoroborate , acetonitrile , copper , adduct , medicinal chemistry , combinatorial chemistry , organic chemistry , polymer chemistry , stereochemistry , amino acid , ionic liquid , biochemistry
The direct asymmetric Mannich reaction of glycine Schiff bases with N ‐tosylimines has been developed with the tetrakis(acetonitrile)copper(I) tetrafluoroborate [Cu(CH 3 CN) 4 BF 4 ]/TF‐BiphamPhos complex. This catalytic system performs well over a broad range of substrates, furnishing anti ‐adducts of various α,β‐diamino acid esters in good yields with up to 94:6 diastereoselectivity and 97% enantioselectivity.