Selective Formation of Adjacent Stereocenters by Allylboration of Ketones under Mild Neutral Conditions | Zendy

Rauful Alam | Zendy; Raducan Mihai | Zendy; Lars Eriksson | Zendy; Kálmán J. Szabó | Zendy

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Selective Formation of Adjacent Stereocenters by Allylboration of Ketones under Mild Neutral Conditions

Author(s) -

Rauful Alam,

Raducan Mihai,

Lars Eriksson,

Kálmán J. Szabó

Publication year - 2013

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol401055m

Subject(s) - stereocenter , chemistry , stereoselectivity , organic chemistry , stereochemistry , catalysis , enantioselective synthesis

Allylboronic acids readily react with a broad variety of ketones, affording homoallylic alcohols with adjacent quaternary and tertiary stereocenters. The reaction proceeds with very high anti stereoselectivity even if the substituents of the keto group have a similar size. α-Keto acids react with syn stereoselectivity probably due to the formation of acyl boronate intermediates. The allylation reactions proceed without added acids/bases under mild conditions. Because of this, many functionalities are tolerated even with in situ generated allylboronic acids.

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