5 years ago

A Highly Stereoselective Synthesis of Tetrahydrofurans

A Highly Stereoselective Synthesis of Tetrahydrofurans
Maik Pahl, Christoph Schneider, Patrick Hoffmeyer, Detlev Belder, Johannes Appun, Isa Kallweit, Michael Boomhoff
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.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201700774

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