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Catalytic asymmetric synthesis of 19,20‐dihydroakuammicine
Author(s) -
Ohori Ken,
Shimizu Satoshi,
Ohshima Takashi,
Shibasaki Masakatsu
Publication year - 2000
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/(sici)1520-636x(2000)12:5/6<400::aid-chir18>3.0.co;2-h
Subject(s) - chemistry , catalysis , enantioselective synthesis , combinatorial chemistry , organic chemistry
An enantiocontrolled total synthesis of 19,20‐dihydroakuammicine using a catalytic asymmetric Michael addition of dimethyl malonate to cyclohexenone as the key step is described. The above catalytic asymmetric Michael addition proceeds quite efficiently in the presence of a heterobimetalic asymmetric catalyst (ALB–KO‐ t ‐Bu–MS 4A, 0.3 mol%), giving the corresponding Michael adduct in 94% yield and 99% ee. Chirality 12:400–403, 2000. © 2000 Wiley‐Liss, Inc.