Tetrahedron Letters p. 61 - 64 (1991)
Update date:2022-08-04
Topics:
Oppolzer, Wolfgang
Starkemann, Christian
Rodriguez, Ines
Bernardinelli, Gerald
O-Silylation of N-propionylsultam 1 provides pure Z O-silyl-N,O-ketene acetal 2 which undergoes Lewis acid promoted addition of aromatic and aliphatic aldehydes to give diastereomerically pure, crystalline "anti" aldols 7 or their silylethers 3. Hydroperoxide-assisted hydrolysis/esterification of products 7 yields enantiomerically pure methoxycarbonyl aldols (11, 12, 13, 14).
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