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Synthesis of 3‐Methylenecyclohexan‐1‐ols by Lewis Acid Catalyzed Cyclization of (Epoxy–allyl)silanes
Author(s) -
Pulido Francisco J.,
Barbero Asunción,
Castreño Pilar
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200901263
Subject(s) - silanes , chemistry , tandem , stereoselectivity , catalysis , epoxy , lewis acids and bases , organic chemistry , silane , materials science , composite material
A new route for the synthesis of (epoxy–allyl)silanes bearing the PhMe 2 Si group has been developed and their acid‐catalyzed cyclization studied. The so‐called normal products derived from 5‐ exo or 6‐ endo attack were never obtained. On the contrary, an interesting tandem rearrangement/cyclization process was observed, which selectively led to 3‐methylenecyclohexan‐1‐ols. A mechanism is proposed to explain this tandem reaction. The stereoselectivity of the cyclization process depends on the nature of the catalyst.