✦ LIBER ✦

Aldol condensations of ethyl 1,3-dithiolane-2-carsoxylate and ethyl 1,3-dithiane-2-carboxylate with chiral aldehydes. Exceptional diastereoface selectivity from two convenient acetate equivalents.

✍ Scribed by Lee A. Flippin; Mark A. Dombroski

Publisher: Elsevier Science
Year: 1985
Tongue: French
Weight: 206 KB
Volume: 26
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)98596-4

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✦ Synopsis

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 Ni28-H2 (EtOH, 20°C). With this mild desulfurization protocol, complete retention of stereochemical integrity was observed for all isolated aldols. Recent reports from Heathcock's laboratory,I and our laboratory,2 have demonstrated that

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