Preparation of Enantiomerically Pure β-Silylcarboxyl Derivatives by Asymmetric 1,4-Addition to N-Enoyl-sultams

DOI: 10.1002/hlca.19860690703

Source and publish data:

Helvetica Chimica Acta p. 1542 - 1545 (1986)

Update date:2022-08-03

Topics:

Authors:

Oppolzer, Wolfgang

Mills, Robert J.

Pachinger, Werner

Stevenson, Thomas

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Article abstract of DOI:10.1002/hlca.19860690703

EtAlCl2-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).

Full text of DOI:10.1002/hlca.19860690703

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