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Stereoselective and Regioselective Pinacol‐Type Rearrangement of a Fused Bicyclic Oxetanol Scaffold
Author(s) -
Melis Nicola,
Luridiana Alberto,
Guillot Régis,
Secci Francesco,
Frongia Angelo,
Boddaert Thomas,
Aitken David J.
Publication year - 2017
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.201701214
Subject(s) - regioselectivity , chemistry , bicyclic molecule , stereoselectivity , pinacol , ether , derivative (finance) , stereochemistry , benzaldehyde , silyl ether , ring (chemistry) , medicinal chemistry , silylation , catalysis , organic chemistry , financial economics , economics
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.