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2004
Cyclopropane derivatives
Q 0021
The Unusual 1,4-Chelation-Controlled Nucleophilic Addition to Aldehydes with
Stereoselectivity. A Systematic Study of Stereoselectivity in the Addition Re47- 063 High
action of Carbon Nucleophiles to cis-Substituted Cyclopropanecarbaldehydes.
— The stereoselectivity in nucleophilic addition reactions to cis-substituted cyclopropanecarbaldehydes (I) is investigated. With a variety of Grignard reagents, high anti-selective additions are observed. The additions occur via an unusual 7-membered
1,4-chelation-controlled pathway. Addition of ZnBr2 further improves the stereoselctivity. Under non-chelation conditions, the syn-products are produced with moderate stereoselectivity. — (KAZUTA, Y.; ABE, H.; YAMAMOTO, T.; MATSUDA, A.;
SHUTO*, S.; Tetrahedron 60 (2004) 31, 6689-6703; Grad. Sch. Pharm. Sci.,
Hokkaido Univ., Sapporo 060, Japan; Eng.) — Bartels
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