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Direct Asymmetric Mannich‐Type Reaction of α‐Isocyanoacetates with Ketimines using Cinchona Alkaloid/Copper(II) Catalysts
Author(s) -
Hayashi Masashi,
Iwanaga Masaru,
Shiomi Noriyuki,
Nakane Daisuke,
Masuda Hideki,
Nakamura Shuichi
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201404629
Subject(s) - cinchona , enantioselective synthesis , chemistry , enantiomer , mannich reaction , catalysis , cinchona alkaloids , organic chemistry , alkaloid , copper , organocatalysis , combinatorial chemistry
The enantioselective direct Mannich‐type reaction of ketimines with α‐isocyanoacetates has been developed. Excellent yields and enantioselectivity were observed for the reaction of various ketimines and α‐isocyanoacetates using cinchona alkaloid/Cu(OTf) 2 and a base. Both enantiomers of the products could be obtained by using pseudoenantiomeric chiral catalysts. This process offers an efficient route for the synthesis of α,β‐diamino acids.