3‐Arylsulfonyloxazolidines as Chiral Templates; Asymmetric Synthesis of 2‐Substituted 2‐Hydroxycyclohexanecarbaldehydes from 2‐Hydroxymethylenecyclohexanone | Zendy

Hoppe Inga | Zendy; Hoppe Dieter | Zendy; Wolff Christian | Zendy; Egert Ernst | Zendy; Herbst Regine | Zendy

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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.

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