Volume 27, Issue 11
Natural Products
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ChemInform Abstract: Catalytic Asymmetrization of meso-3,7-Bis(siloxy)cycloheptene by Chiral Rhodium(I)-binap (2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl) Catalyst: The Enantiocontrolled Asymmetric Synthesis of (-)-(S)- Physoperuvine.

K. HIROYA

K. HIROYA

Pharm. Inst., Tohoku Univ., Aobayama, Sendai 980-77, Japan

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K. OGASAWARA

K. OGASAWARA

Pharm. Inst., Tohoku Univ., Aobayama, Sendai 980-77, Japan

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First published: March 12, 1996

Abstract

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ChemInform Abstract

Catalytic asymmetrization of the meso-bis(siloxy)cycloheptene (I) in the presence of a chiral rhodium (I)-BINAP catalyst provides the optically active siloxy ketone (cf. (II)) in ca. 70% e.e. after hydrolytic work-up. The (R)-enantiomer, obtained using the corresponding Rh-(R)-BINAP-catalyst, can be readily transformed into the alkaloid (S)-physoperuvine (V).

chemical structure image

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