Tetrahedron Letters p. 3309 - 3312 (1994)
Update date:2022-08-03
Topics:
Agami, Claude
Couty, Francois
Lequesne, Christelle
Diastereoisomerically pure N-Boc 2-acyloxazolidines were synthesized from phenylglyoxal and ethyl glyoxylate.Reaction of these heterocycles with Grignard reagents is highly stereoselective.Homochiral 1,2-diols were ultimately obtained after N-deprotection, hydrolysis and reduction of the intermediate α-hydroxy aldehyde.The asymmetric induction can be explained by a chelated model.
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Doi:10.1016/S0040-4020(01)85643-X
(1994)Doi:10.1021/jo00087a054
(1994)Doi:10.1039/c39940000831
(1994)Doi:10.1016/S0040-4039(00)73051-6
(1994)Doi:10.1002/chem.200902172
(2009)Doi:10.1134/S1070363214010095
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