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Asymmetric induction of four chiral centers by hetero Diels‐Alder reaction of a chiral nitroso dienophile
Author(s) -
Werbitzky Oleg,
Klier Konrad,
Felber Helena
Publication year - 1990
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199019900148
Subject(s) - asymmetric induction , chemistry , nitroso , yield (engineering) , diels–alder reaction , cleavage (geology) , absolute configuration , medicinal chemistry , stereochemistry , enantioselective synthesis , organic chemistry , catalysis , physics , materials science , fracture (geology) , composite material , thermodynamics
The Diels‐Alder reaction of cis ‐5,6‐diacetoxy‐1,3‐cyclohexadiene ( 1 ), which has a meso configuration, with the chiral nitroso dienophile 2 occurs with induction of four asymmetric centers in very high optical yield (ee = 94%) and leads to the dihydro oxazine 3 (89%). The influence of the reaction temperature on the asymmetric induction was investigated and the absolute configuration of the product determined. Reductive cleavage of the N O bond of 3 presents a simple route to enantiomerically pure derivatives of (1 R )‐conduramine A1 (82%).