DIASTEREOSELECTIVE DOUBLE MICHAEL ADDITIONS OF VINYLOGOUS ESTERS AND THEXYLDIMETHYLSILYL TRIFLATE-INDUCED CYCLIZATIONS

DOI: 10.1016/S0040-4039(00)92283-4

Source and publish data:

Tetrahedron Letters p. 4691 - 4694 (1991)

Update date:2022-08-05

Topics:

Authors:

Schinzer, Dieter

Kalesse, Markus

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Article abstract of DOI:10.1016/S0040-4039(00)92283-4

Double Michael additions of vinylogous esters of type 1 with crotyl ester generates diastereoselectively bicyclo<2.2.2>octanone 2 with four defined chiral centers via a synclinal transition state.Thexyldimethylsilyl enol ethers of type 5 and 10 undergo smooth cyclization to bicyclo<3.3.1>nonenones 7 and bicyclo<3.3.0>octenones 12 by addition of Lewis acids.

Full text of DOI:10.1016/S0040-4039(00)92283-4

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