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2005
Sulfoxides
Q 0600
03- 101
Asymmetric Intramolecular Michael Addition of α-Sulfinyl Vinylic Carbanion to
Enoates. — The title reaction of carbanions derived from (R)-tolylsulfinyl enoates proceeds with excellent selectivity. (Z)-Configuration of the enoate is essential to achieve
high diastereoselectivity. Enoates leading to cyclopentene derivatives afford the products with (R)-configuration at the newly formed asymmetric carbon atom, whereas reversed selectivity is observed in the cyclohexene formation. The enolates can be
trapped with alkyl halides and benzaldehyde with formation of two or three contiguous
stereocenter in a one-pot reaction in a diastereoselective manner. — (MAEZAKI, N.;
SAWAMOTO, H.; YUYAMA, S.; YOSHIGAMI, R.; SUZUKI, T.; IZUMI, M.;
OHISHI, H.; TANAKA*, T.; J. Org. Chem. 69 (2004) 19, 6335-6340; Grad. Sch.
Pharm. Sci., Osaka Univ., Suita, Osaka 565, Japan; Eng.) — Klein
2005
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