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Catalytic Enantioselective Aza Diels–Alder Reactions of Imino Dienophiles
Author(s) -
Yao Sulan,
Johannsen Mogens,
Hazell Rita G.,
Jørgensen Karl Anker
Publication year - 1998
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19981204)37:22<3121::aid-anie3121>3.0.co;2-j
Subject(s) - enantioselective synthesis , catalysis , chemistry , diels–alder reaction , adduct , conjugated system , copper , organic chemistry , medicinal chemistry , combinatorial chemistry , polymer
Abstract 1 mol% of catalyst is sufficient : The hetero Diels–Alder reaction of α ‐imino esters 1 with activated conjugated dienes 2 (R=H, Me) needs only 1 mol% of a 2,2′‐bis(diarylphosphanyl)‐1,1′‐binaphthyl (BINAP) copper( I ) complex as the catalyst to generate the adducts 3 in good yields and with enantioselectivities up to 96%. The reaction can also be carried out on gram scale! Tos=H 3 CC 6 H 4 SO 2 ; TMS=Me 3 Si.