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A Highly Stereoselective Synthesis of Tetrahydrofurans

Abstract

The development of a direct and highly stereoselective synthesis of 2,3,5‐substituted tetrahydrofurans has been accomplished through a combination of batch‐ and microchip‐MS‐experiments. This sequential transformation comprises a Lewis acid‐mediated reaction of bis(silyl) dienediolate 1 and a broad range of aldehydes, furnishing products with three new σ‐bonds and three stereogenic centers in a one‐pot process with typically good yields and excellent stereoselectivity. Key steps which have been elucidated primarily with microchip‐MS‐experiments include a vinylogous aldol reaction and a Prins‐type cyclization. Furthermore, a titanium BINOL complex is a powerful chiral catalyst for this process. The products were further converted into bi‐ and tricylic products by carbonyl–ene reactions, proceeding with excellent yields and diastereoselectivity.

A one‐pot tetrahydrofuran synthesis employing a bis(silyl) dienediolate and two aldehydes has been developed. This sequential process furnishes a broad range of 2,3,5‐substituted tetrahydrofurans with good yields and typically as single diastereomers. It can be rendered enantioselective using a chiral titanium catalyst.

Autoren:   Johannes Appun, Michael Boomhoff, Patrick Hoffmeyer, Isa Kallweit, Maik Pahl, Detlev Belder, Christoph Schneider
Journal:   Angewandte Chemie International Edition
Jahrgang:   2017
Seiten:   n/a
DOI:   10.1002/anie.201700774
Erscheinungsdatum:   09.05.2017
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