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3‐Arylsulfonyloxazolidines as Chiral Templates; Asymmetric Synthesis of 2‐Substituted 2‐Hydroxycyclohexanecarbaldehydes from 2‐Hydroxymethylenecyclohexanone
Author(s) -
Hoppe Inga,
Hoppe Dieter,
Wolff Christian,
Egert Ernst,
Herbst Regine
Publication year - 1989
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198900671
Subject(s) - stereocenter , carbanion , sulfamide , aldehyde , enantioselective synthesis , oxazolidine , chemistry , stereochemistry , enol , selectivity , cleavage (geology) , condensation , organic chemistry , catalysis , materials science , physics , fracture (geology) , composite material , thermodynamics
Two new stereogenic centers are formed upon condensation of the sulfamide 1 with the enol 2 to give the oxazolidine 3 , which, in turn, adds carbanion derivatives MNu with high diastereofacial selectivity to give 4 . Cleavage of the chiral auxiliary with 1,3‐propanedithiol leads to diastereo‐ and enantiomerically pure aldehyde derivatives 5 . All steps proceed practically stereo specifically.