Asymmetric cyclopropanation by reaction of a γ-chloromethylated chiral vinylic sulfoxide with allylmagnesium bromide

DOI: 10.1248/cpb.43.571

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 571 - 577 (1995)

Update date:2022-08-05

Topics:

Authors:

Takemoto

Ohra Ohra

Sugiyama

Imanishi

Iwata Iwata

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Article abstract of DOI:10.1248/cpb.43.571

An optically active vinylic sulfoxide bearing a leaving group at the γ-position was stereoselectively transformed into a chiral cyclopropane by means of a Michael addition with an allylmagnesinm bromide. The Michael induced ring-closure reaction requires both allylmagnesium bromide as a nucleophile and chloride as a leaving group for high diastereoselectivity. The absolute stereochemistry of the cycloadduct was confirmed by X-ray analysis.

Full text of DOI:10.1248/cpb.43.571

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