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Stereoselective Synthesis of 2,3,5-Trisubstituted Tetrahydrofurans Initiated by a Titanium–BINOLate-Catalyzed Vinylogous Aldol Reaction

Author:
Hoffmeyer, Patrick, Schneider, Christoph
Source:
Journal of organic chemistry 2018 v.84 no.2 pp. 1079-1084
ISSN:
1520-6904
Subject:
aldehydes, catalysts, chemical reactions, chemical structure, enantioselective synthesis, organic chemistry, tetrahydrofuran
Abstract:
The enantioselective synthesis of 2,3,5-trisubstituted tetrahydrofurans 3 has been achieved using a chiral titanium–BINOL complex as catalyst for the vinylogous Mukaiyama aldol reaction of bis(silyl) diendiolate 1 and an aldehyde. The ensuing BF₃·OEt₂-mediated Prins-type cyclization with a second aldehyde gave rise to 2,3,5-substituted tetrahydrofurans 3 with generally good yields and excellent stereocontrol. In this process, three new σ-bonds and three new stereogenic centers were generated in a one-pot process.
Agid:
6271503