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Stereoselective and Regioselective Pinacol-Type Rearrangement of a Fused Bicyclic Oxetanol Scaffold.

Authors :
Melis, Nicola
Luridiana, Alberto
Guillot, Régis
Secci, Francesco
Frongia, Angelo
Boddaert, Thomas
Aitken, David J.
Source :
European Journal of Organic Chemistry; 10/25/2017, Vol. 2017 Issue 39, p5896-5902, 7p
Publication Year :
2017

Abstract

The Paternò-Büchi reaction between benzaldehyde and trimethylsilyloxycyclopentene gave access to an unprecedented silyl ether derivative of 6-oxabicyclo[3.2.0]heptan-1-ol. The bicyclic structure underwent selective reductive ring opening and acid-catalyzed pinacol-type rearrangement reactions with complete regioselectivity, accompanied by moderate to excellent mechanism-dependent diastereoselectivity. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
1434193X
Volume :
2017
Issue :
39
Database :
Complementary Index
Journal :
European Journal of Organic Chemistry
Publication Type :
Academic Journal
Accession number :
125932594
Full Text :
https://doi.org/10.1002/ejoc.201701214