Enantioselective Intramolecular C–H Insertion Reactions of Donor–Donor Metal Carbenoids | Zendy

Cristian Soldi | Zendy; Kellan N. Lamb | Zendy; Richard A. Squitieri | Zendy; Marcos GonzálezLópez | Zendy; Michael J. Di Maso | Zendy; Jared T. Shaw | Zendy

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Enantioselective Intramolecular C–H Insertion Reactions of Donor–Donor Metal Carbenoids

Author(s) -

Cristian Soldi,

Kellan N. Lamb,

Richard A. Squitieri,

Marcos GonzálezLópez,

Michael J. Di Maso,

Jared T. Shaw

Publication year - 2014

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/ja508586t

Subject(s) - chemistry , intramolecular force , enantioselective synthesis , insertion reaction , metal , stereochemistry , medicinal chemistry , catalysis , organic chemistry

The first asymmetric insertion reactions of donor-donor carbenoids, i.e., those with no pendant electron-withdrawing groups, are reported. This process enables the synthesis of densely substituted benzodihydrofurans with high levels of enantio- and diastereoselectivity. Preliminary results show similar efficiency in the preparation of indanes. This new method is used in the first enantioselective synthesis of an oligoresveratrol natural product (E-δ-viniferin).

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