Synergistic Rhodium/Phosphoric Acid Catalysis for the Enantioselective Addition of Oxonium Ylides to  ortho ‐Quinone Methides | Zendy

Alamsetti Santosh Kumar | Zendy; Spanka Matthias | Zendy; Schneider Christoph | Zendy

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Synergistic Rhodium/Phosphoric Acid Catalysis for the Enantioselective Addition of Oxonium Ylides to ortho ‐Quinone Methides

Author(s) -

Alamsetti Santosh Kumar,

Spanka Matthias,

Schneider Christoph

Publication year - 2016

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201509247

Subject(s) - oxonium ion , chemistry , stereocenter , enantioselective synthesis , rhodium , ylide , phosphoric acid , brønsted–lowry acid–base theory , catalysis , combinatorial chemistry , medicinal chemistry , organic chemistry , ion

We report herein a powerful and highly stereoselective protocol for the domino‐type reaction of diazoesters with ortho ‐quinone methides generated in situ to furnish densely functionalized chromans with three contiguous stereogenic centers. A transition‐metal and a Brønsted acid catalyst were shown to act synergistically to produce a transient oxonium ylide and ortho ‐quinone methide, respectively, in two distinct cycles. These intermediates underwent subsequent coupling in a conjugate‐addition–hemiacetalization event in generally good yield with excellent diastereo‐ and enantioselectivity.

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