Stereoselective and Regioselective Pinacol‐Type Rearrangement of a Fused Bicyclic Oxetanol Scaffold. Issue 39 (18th October 2017)

• Record Type: Journal Article
• Authors: Melis, Nicola; Luridiana, Alberto; Guillot, Régis; Secci, Francesco; Frongia, Angelo; Boddaert, Thomas; Aitken, David J.
• Is Part Of: European journal of organic chemistry. Issue 39(2017)
• Page Start: 5896
• Page End: 5902
• Publication Date: 2017-10-18
• Subjects: Lewis acids -- Synthetic methods -- Paternò‐Büchi reaction -- Photochemistry -- Rearrangement; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201701214
• Languages: English
• ISSNs: 1434-193X

Abstract

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 : 6‐Oxabicyclo[3.2.0]heptan‐1‐ol derivatives, obtained by an efficient photochemical Paternò‐Büchi reaction, were used in a regio‐ and stereoselective Lewis acid catalyzed pinacol‐type rearrangement reaction.