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Synthesis of 2-vinyl-1,3-diols via highly stereoselective reduction of 2-vinyl aldols using trimethylsilyl stereo-directing group

✍ Scribed by Keisuke Suzuki; Masato Shimazaki; Gen-ichi Tsuchihashi

Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
228 KB
Volume
27
Category
Article
ISSN
0040-4039

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✦ Synopsis

are synthesized by the reductign of aldol derivatives bearing a-trimethylsilylvinyl group at C(2) (LiBEt3H / THF, -78 C), which proceeds highly stereoselectively to give 1,2-syn isomer as the sole product.

📜 SIMILAR VOLUMES

Stereo-divergent asymmetric total synthe
Stereo-divergent asymmetric total synthesis of avenaciolide and isoavenaciolide. Complete reversal of stereoselectivity in reduction of 2-vinyl aldols with / without trimethylsilyl directing group
✍ Keisuke Suzuki; Mayumi Miyazawa; Masato Shimazaki; Gen-ichi Tsuchihashi 📂 Article 📅 1986 🏛 Elsevier Science 🌐 French ⚖ 253 KB

## Stereo-divergent asymmetric total synthesis of avenaciolide and isoavenaciolide was achieved via 1.2-rearrangement of chiral epoxyalcohol derivatives. where complete reversal of stereoselectivity with / without the TMS-directing group in the reduction of Z-vinyl aldols was used as the key branc