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Synthesis of stereodefined vinyl-tetrahydropyran and vinyl-octahydrochromene derivatives via acetalization–cyclization of allylsilanes with aldehydes. Origin of the high stereoselectivity

✍ Scribed by Johan Kjellgren; Kálmán J. Szabó

Book ID
104232380
Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
157 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

Functionalized allylsilanes 1-5 and aldehydes 6-8 undergo Lewis-acid mediated ring closure to afford 2,3,5-or 6-substituted tetrahydropyrans (8-15) and 2,3-substituted octahydrochromenes (16a-b) with excellent stereoselectivity. According to DFT calculations the high stereoselectivity arises from electronically induced steric effects occurring in the key-intermediate of the cyclization.

📜 SIMILAR VOLUMES

ChemInform Abstract: Synthesis of Stereo
ChemInform Abstract: Synthesis of Stereodefined Vinyl-tetrahydropyran and Vinyl-octahydrochromene Derivatives via Acetalization—Cyclization of Allylsilanes with Aldehydes. Origin of the High Stereoselectivity.
✍ Johan Kjellgren; Kalman J. Szabo 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 30 KB

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