Preparation of Enantiomerically Pure β‐Silylcarboxyl Derivatives by Asymmetric 1,4‐Addition to  N ‐Enoyl‐sultams. Preliminary Communication | Zendy

Oppolzer Wolfgang | Zendy; Mills Robert J. | Zendy; Pachinger Werner | Zendy; Stevenson Thomas | Zendy

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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

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).

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