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KMID : 0043319910140040364
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Archives of Pharmacal Research
1991 Volume.14 No. 4 p.364 ~ p.369
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Regio- and Stereoselective Reactions of (S)-(1-Methylpyrrolidin-2-yl)methyl Allyl Sulfide
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Park HK
Baik NH/Lee JY/Kim SJ/Ham WH
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Abstract
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The synthesis and regioselective reactions of a chiral allyl sulfide, (S)-(+)-(1-methylpyrrolidin-2-yl)methyl allyl sulfide (MAS, 1) are described. Remarkable alpha-regioselectivity was observed in the alkylation of the carbanion of MAS while 1:3 mixtures of alpha-and gammar-adducts were produced in the addition of the MAS anion to aldehydes. However, a dramatic change of the regioselectivity was witnessed when Lewis acids such as Et3Al, Et3B, and Ti(OiPr)4 were used as additives in the addition reaction. In these cases, alpha-adducts were formed exclusively. A rationale for the change of regioselectivity is provided. And the stereochemical aspect of the addition reaction is also described.
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KEYWORD
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