In addition to organic halides, alkyl tosylates (R'OTs. Section 9.13) also react with organocuprates (R2CuLi) to form coupling products R – R'. When 2° alkyl tosylatee are used as starting materials (R2CHOTs), inversion of the configuration at a stereogenic center results. Keeping this in mind, draw the product formed when each compound is treated with (CH3)2CuLi.

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter10: Alcohols
Section: Chapter Questions
Problem 10.57P
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In addition to organic halides, alkyl tosylates (R'OTs. Section 9.13) also react with organocuprates (R2CuLi) to form coupling products R – R'. When 2° alkyl tosylatee are used as starting materials (R2CHOTs), inversion of the configuration at a stereogenic center results. Keeping this in mind, draw the product formed when each compound is treated with (CH3)2CuLi.

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