有機合成化学協会誌
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
キラルルイス酸オキサザボロリジノンによる不斉アルドール反応の展開
清岡 俊一
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ジャーナル フリー

1997 年 55 巻 4 号 p. 313-324

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Reaction of N-sulfonyl amino acid with 1 equiv. of BH3 THF easily gave the oxazaborolidinone which promoted the aldol reaction of a variety of aldehydes with silyl ketene acetals with very high enantioselectivity. For example, isobutyrate aldols were obtained with >96% ee and acetate aldols were obtained with >98% ee by using a silyl nucleophile derived from ethyl 1, 3-dithiolane-2-carboxylate. The level of the selectivity is surely acceptable for practical syntheses although the promoter is used as stoichiometric amounts. The scope and limitation of the oxazaborolidinone-promoted aldol reaction will be discussed by surveying the stereochemical outcome of the reaction inducing the high enantioselectivity.

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