Asymmetric Heck Reactions via Neutral Intermediates: Enhanced Enantioselectivity with Halide Additives Gives Mechanistic Insights | Zendy

Overman Larry E. | Zendy; Poon Daniel J. | Zendy

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Asymmetric Heck Reactions via Neutral Intermediates: Enhanced Enantioselectivity with Halide Additives Gives Mechanistic Insights

Author(s) -

Overman Larry E.,

Poon Daniel J.

Publication year - 1997

Publication title -

angewandte chemie international edition in english

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 0570-0833

DOI - 10.1002/anie.199705181

Subject(s) - binap , iodide , halide , chemistry , trifluoromethanesulfonate , enantioselective synthesis , catalysis , medicinal chemistry , photochemistry , organic chemistry

Both phosphorus atoms of the bis(phosphane) BINAP and the iodide ion are bound to Pd during the enantioselective step of the asymmetric Heck cyclization of iodide 1 . This is the conclusion of an investigation of the halide effect on Pd‐( R )‐BINAP‐catalyzed cyclization of triflate 2 and the cyclization of iodide 1 with Pd‐( R )‐ 3 , a model for a monocoordinated Pd‐BINAP catalyst. BINAP‐catalyzed reaction with 1 —or 2 in the presence of Cl ‐ , Br ‐ , or I ‐ —proceeds to give 4 with an ee value of greater than 90%. PMP = 1,2,2,6,6‐pentamethylpiperidine.

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