Cyclopropanation of protected chiral, acyclic allylic alcohols: Expedient access to the anti-cyclopropylcarbinol derivatives

Organic Letters

Volumn 4, Issue 20, 2002, Pages 3351-3353

  Charette, André B ^a   Lacasse, Marie Christine ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

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ARTICLE;

EID: 0038275090     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0264051     Document Type: Article

References (24)

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23. Reaction of a bulkier allylic tert-buryldiphenylsilyl ether led mostly to decomposition of the starting material, which in this case probably occurs faster than the cyclopropanation under these Lewis-acidic conditions.
24. The sense of induction appears to be highly dependent upon the nature of the alkene substituent. It has been observed that the cyclopropanation of a β-chloro allylic ethers under the conditions reported here led preferentially to the syn diastereoisomer: Evans, D. A.; Burch, J. D. Org. Lett. 2001, 3, 503.