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Preparation of Enantiomerically Pure β‐Silylcarboxyl Derivatives by Asymmetric 1,4‐Addition to N ‐Enoyl‐sultams. Preliminary Communication
Author(s) -
Oppolzer Wolfgang,
Mills Robert J.,
Pachinger Werner,
Stevenson Thomas
Publication year - 1986
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19860690703
Subject(s) - chemistry , oxidative cleavage , propionate , camphor , conjugated system , reagent , organic chemistry , cleavage (geology) , silylation , stereochemistry , medicinal chemistry , catalysis , geotechnical engineering , fracture (geology) , engineering , polymer
Abstract EtAlCl 2 ‐promoted additions of organocopper reagents to camphor‐derived, conjugated N ‐enoyl‐sultams gave saturated and olefinic β‐silylcarboxyl derivatives with high diastereodifferentiation. Nondestructive removal of the chiral auxiliary followed by oxidative Si‐C bond cleavage furnished enantiomerically pure acetate‐derived aldols and propionate‐derived ‘ anti ’ ‐aldols ( via silyl‐directed α‐methylation).