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

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 :...

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Published inChemical communications (Cambridge, England) Vol. 48; no. 74; pp. 9230 - 9232
Main Authors Aggarwal, Varinder K., Ball, Liam T., Carobene, Simon, Connelly, Rickki L., Hesse, Matthew J., Partridge, Benjamin M., Roth, Philippe, Thomas, Stephen P., Webster, Matthew P.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2012
Subjects
Boron - chemistry
Chemistry
Chemistry Techniques, Synthetic
Chemistry, Multidisciplinary
Kinetics
Lithium - chemistry
Natural products
Oxidation
Physical Sciences
Science & Technology
Sesquiterpenes - chemical synthesis
Sesquiterpenes - chemistry
Stereoisomerism
Substrate Specificity
Synthesis
TERTIARY BORONIC ESTERS
SECONDARY ALCOHOLS
ROUTE
METHODOLOGY
CONVERSION
PROTODEBORONATION
(R)-(-)-CURCUPHENOL
(+)-CURCUPHENOL
(-)-CURCUQUINONE
(S)-(+)-CURCUPHENOL
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Summary: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.
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ISSN:1359-7345
1364-548X
DOI:10.1039/c2cc32176a