Control of Chemo-, Regio-, and Enantioselectivity in Copper Hydride Reductions of Morita–Baylis–Hillman Adducts
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- 作者：Roscoe T. H. Linstadt ; Carl. A. Peterson ; Carina I. Jette ; Zarko V. Boskovic ; Bruce H. Lipshutz
- 刊名：Organic Letters
- 出版年：2017
- 出版时间：January 20, 2017
- 年：2017
- 卷：19
- 期：2
- 页码：328-331
- 全文大小：386K
- ISSN：1523-7052
文摘
Nonracemically ligated copper hydride can be used to effect tandem SN2′/1,2-reductions of racemic Morita–Baylis–Hillman (MBH) acetates to access enantioenriched chiral allylic alcohols with defined olefin geometry. MBH esters, including those with β-substitution, can be transformed to stereodefined enoates by taking advantage of a bulky, oligomeric, in situ generated trialkoxysiloxane leaving group. Finally, an atypical conversion of easily arrived at MBH alcohol derivatives to nonracemic allylic alcohols is disclosed.