Substrate‐Controlled Highly Diastereoselective Synthesis of Primary and Secondary Diorganozinc Reagents by a Hydroboration/Boron–Zinc Exchange Sequence | Zendy

Hupe Eike | Zendy; Calaza M. Isabel | Zendy; Knochel Paul | Zendy

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Substrate‐Controlled Highly Diastereoselective Synthesis of Primary and Secondary Diorganozinc Reagents by a Hydroboration/Boron–Zinc Exchange Sequence

Author(s) -

Hupe Eike,

Calaza M. Isabel,

Knochel Paul

Publication year - 2003

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.200204662

Subject(s) - hydroboration , chemistry , reagent , zinc , electrophile , substrate (aquarium) , boron , combinatorial chemistry , organic chemistry , primary (astronomy) , catalysis , oceanography , physics , astronomy , geology

The scope of substrate‐controlled diastereoselective hydroborations can be considerably enhanced by a boron–zinc exchange reaction, providing organozinc derivatives that react with a broad range of electrophiles. Even normally unreactive boronic esters, obtained by Rh‐catalyzed hydroboration with catecholborane, react readily with i Pr 2 Zn providing the corresponding zinc reagents in high diastereoselectivity.

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