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- W2950634476 abstract "Optically active tertiary alcohols bearing a carbonyl function at the α-position were synthesized enantioselectively by using chiral 1,3-oxathianes, 1,3-oxazines or 1,3-oxazolidines.1,2,3 The tertiary alcohols were generally prepared by the reaction of 2-acyl derivatives with organometallics. Among the heterocycles, 2-acyl-1,3-oxathianes have been extensively studied to examine the diastereoselection.1,2 In the reaction of 2-acyl-1,3-oxathianes or perhydro-2acyl-1,3-oxazines with organometallics, the stereoselectivities support the assumption that chelation of an organometallic reagent between the carbonyl oxygen and the ether oxygen of the ring is necessary for a high degree of asymmetric induction. However, some results were different among 1,3-oxathianes, 1,3-oxazines, and 1,3-oxazolidines depending on the nature of organometallics, reducing agents, and the presence of Lewis acids.1,2,3 Recently we and other group have synthesized chiral 2piperidineacetates, which were readily converted to chiral 2piperidineethanols.4,5 The 2-piperidineethanols may be utilized as chiral auxiliaries to prepare optically active compounds, since chiral amino alcohols or amino thiols have been used in many asymmetric reactions.6 In this paper, we describe the diastereoselectivity in the reaction of chiral perhydro-2-acyl-1,3-oxazines, derived from 2-piperidineethanols, with organometallics or reducing agents." @default.
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- W2950634476 date "1999-01-01" @default.
- W2950634476 modified "2023-09-26" @default.
- W2950634476 title "AN ASYMMETRIC SYNTHESIS OF ALCOHOLS USING CHIRAL 2-PIPERIDINEETHANOLS" @default.
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