Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5221435 | Tetrahedron | 2011 | 9 Pages |
Abstract
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.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Gopal Sirasani, Tapas Paul, Rodrigo B. Andrade,