ALDOL CONDENSATIONS OF ETHYL 1,3-DITHIOLANE-2-CARBOXYLATE AND ETHYL 1,3-DITHIANE-2-CARBOXYLATE WITH CHIRAL ALDEHYDES. EXCEPTIONAL DIASTEREOFACE SELECTIVITY FROM TWO CONVENIENT ACETATE EQUIVALENTS.

DOI: 10.1016/S0040-4039(00)98596-4

Source and publish data:

Tetrahedron Letters p. 2977 - 2980 (1985)

Update date:2022-08-03

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Authors:

Flippin, Lee A.

Dombroski, Mark A.

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Article abstract of DOI:10.1016/S0040-4039(00)98596-4

Lithium enolates derived from the title esters show high diastereoface selectivity in their reactions with chiral aldehydes.The resulting 2,2-dithioaldols are desulfurized in good yield with Ni2B-H2 (EtOH, 20 deg C).With this mild desulfurization protocol, complete retention of stereochemical integrity was observed for all isolated aldols.

Full text of DOI:10.1016/S0040-4039(00)98596-4

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