Chiral silicon compounds II: The asymmetric reaction of a chiral allysilane with aldehydes

Abstract

The chiral allylsilane I was prepared from (-)-b-pinene and was assigned to have 1S, 2S, 5S stereochem. The reactions of I with a no. of aldehydes were found to give chiral homoallylic alcs. with modest enantioselectivity. More importantly, enantioselectivity was found to be dependent on the Lewis acid used. With TiCl4, the absolute configuration of the chiral homoallylic alcohol is consistently R, on the other hand with SnCl4 or BF3-OEt2 oppositely S. The reaction was used to synthesize optically active 4-octyl-g-butyrolactone (II).

Key words: SUBSTITUTION REACTION, ALDEHYDES, ORGANO SILICON COMPOUNDS, SILANE P, INSECT HORMONE, ALLYL GROUP, CHIRALITY, PINENE, ELECTROPHILIC REACTION

CLC Number:

O627

Cite this article

YI GUOLIANG;WANG DONG;CHEN DEHENG. Chiral silicon compounds II: The asymmetric reaction of a chiral allysilane with aldehydes[J]. Chin. J. Org. Chem., 1988, 8(2): 115-120.

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