Sequencing cross-metathesis and non-metathesis reactions to rapidly access building blocks for synthesis

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• 作者：Gopal Sirasanip>ap> ; Tapas Paulp>ap> ; Rodrigo B. Andradep> ; p>p>ap>p> ; p>p>randrade@temple.edup>
• 关键词：One-pot ; Tandem ; Cross-metathesis ; Olefination ; 2 ; 4-Dienoates ; trans Allylic alcohols ; Evans aldol ; Brown allylboration ; Roush crotylboration
• 刊名：Tetrahedron
• 出版年：2011
• 出版时间：25 March 2011
• 年：2011
• 卷：67
• 期：12
• 页码：2197-2205
• 全文大小：1378 K

文摘

The olefin cross-metathesis reaction has been sequenced with four common organic transformations in a one- or two-pot manner to rapidly access useful building blocks. Those reactions are: (1) phosphorus-based olefination (e.g., Wittig and Horner–Wadsworth–Emmons); (2) hydride reduction; (3) Evans propionate aldol reaction; (4) Brown allyl- and Roush crotyl-boration. The products of these reactions include stereodefined 2,4-dienoates, trans allylic alcohols, syn-propionate aldols, and chiral non-racemic homoallylic alcohols, respectively. Many of these intermediates have been carried further to natural products, demonstrating the utility of the methodology.