Synthesis of Tertiary Allylboronates from Vinylboronates

Brian A. Ondrusek; Jin Kyoon Park; D. Tyler McQuade

doi:10.1055/s-0033-1340282

Synlett, Table of Contents

Synlett 2014; 25(2): 239-242
DOI: 10.1055/s-0033-1340282

letter

Synthesis of Tertiary Allylboronates from Vinylboronates

Brian A. Ondrusek

^aFlorida State University, Department of Chemistry and Biochemistry, Tallahassee, Florida 32306-4390, USA Fax: +1(850)6648281 Email: mcquade@chem.fsu.edu

,

Jin Kyoon Park

^bDepartment of Chemistry and Chemical Institute for Functional Materials, Pusan National University, Busan 609-735, Republic of Korea

,

D. Tyler McQuade*

^aFlorida State University, Department of Chemistry and Biochemistry, Tallahassee, Florida 32306-4390, USA Fax: +1(850)6648281 Email: mcquade@chem.fsu.edu

› Author Affiliations

Abstract

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Abstract

Allylic boronates are versatile intermediates in organic synthesis. Herein, we present an ‘ate-mediated allylic substitution’ (AMAS) approach to allylic boronates. Bifunctional vinylboroate/ allylic acetate esters react with Grignard reagents to form tertiary allylic boronates via an AMAS reaction. We demonstrate that the method tolerates a wide range of substrates and Grignard reagents.

Key words

boron - homogeneous catalysis - copper - organometallic reactions - allylation

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References

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14 The results of such an oxidation to yield a tertiary allylic alcohol are included in the Supporting Information. Compounds not found within the text are numbered sequentially beginning with 9.
15 A mechanistic rationale for E-selectivity is included in the Supporting Information.

Supplementary Material

Supporting Information