Application of the lithiation–borylation reaction to the rapid and enantioselective synthesis of the bisabolane family of sesquiterpenes

Varinder K. Aggarwal; Liam T. Ball; Simon Carobene; Rickki L. Connelly; Matthew J. Hesse; Benjamin M. Partridge; Philippe Roth; Stephen P. Thomas; Matthew P. Webster

doi:10.1039/c2cc32176a

Application of the lithiation–borylation reaction to the rapid and enantioselective synthesis of the bisabolane family of sesquiterpenes

Varinder K. Aggarwal, Liam T. Ball, Simon Carobene, Rickki L. Connelly, Matthew J. Hesse, Benjamin M. Partridge, Philippe Roth, Stephen P. Thomas, Matthew P. Webster

Research output: Contribution to journal › Article › peer-review

Abstract

The expedient enantioselective synthesis of 5 bisabolane sesquiterpenes has been achieved using a common, one-pot lithiation-borylation reaction of secondary benzylic carbamates and either protodeboronation or oxidation to give the natural products in fewer than 5 steps, with high yield and >94 : 6 er.

Original language	English
Pages (from-to)	9230-9232
Number of pages	3
Journal	Chemical Communications
Volume	48
Issue number	74
DOIs	https://doi.org/10.1039/c2cc32176a
Publication status	Published - 25 Sept 2012

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title = "Application of the lithiation–borylation reaction to the rapid and enantioselective synthesis of the bisabolane family of sesquiterpenes",

abstract = "The expedient enantioselective synthesis of 5 bisabolane sesquiterpenes has been achieved using a common, one-pot lithiation-borylation reaction of secondary benzylic carbamates and either protodeboronation or oxidation to give the natural products in fewer than 5 steps, with high yield and >94 : 6 er.",

author = "Aggarwal, {Varinder K.} and Ball, {Liam T.} and Simon Carobene and Connelly, {Rickki L.} and Hesse, {Matthew J.} and Partridge, {Benjamin M.} and Philippe Roth and Thomas, {Stephen P.} and Webster, {Matthew P.}",

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T1 - Application of the lithiation–borylation reaction to the rapid and enantioselective synthesis of the bisabolane family of sesquiterpenes

AU - Aggarwal, Varinder K.

AU - Ball, Liam T.

AU - Carobene, Simon

AU - Connelly, Rickki L.

AU - Hesse, Matthew J.

AU - Partridge, Benjamin M.

AU - Roth, Philippe

AU - Thomas, Stephen P.

AU - Webster, Matthew P.

PY - 2012/9/25

Y1 - 2012/9/25

N2 - The expedient enantioselective synthesis of 5 bisabolane sesquiterpenes has been achieved using a common, one-pot lithiation-borylation reaction of secondary benzylic carbamates and either protodeboronation or oxidation to give the natural products in fewer than 5 steps, with high yield and >94 : 6 er.

AB - The expedient enantioselective synthesis of 5 bisabolane sesquiterpenes has been achieved using a common, one-pot lithiation-borylation reaction of secondary benzylic carbamates and either protodeboronation or oxidation to give the natural products in fewer than 5 steps, with high yield and >94 : 6 er.

U2 - 10.1039/c2cc32176a

DO - 10.1039/c2cc32176a

M3 - Article

SN - 1359-7345

VL - 48

SP - 9230

EP - 9232

JO - Chemical Communications

JF - Chemical Communications

IS - 74

ER -

Application of the lithiation–borylation reaction to the rapid and enantioselective synthesis of the bisabolane family of sesquiterpenes

Abstract

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