Enantioselective Construction of Quaternary Stereogenic Centers from Tertiary Boronic Esters: Methodology and Applications

Pin it down: A range of substrates that bear versatile functional groups with quaternary stereogenic centers have been prepared with very high enantioselectivity from tertiary boronic esters (see scheme; Cb=N,N‐diisopropylcarbamoyl, pin=pinacolato). The preparation of allylboronic esters bearing con...

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Published inAngewandte Chemie (International ed.) Vol. 50; no. 16; pp. 3760 - 3763
Main Authors Sonawane, Ravindra P., Jheengut, Vishal, Rabalakos, Constantinos, Larouche-Gauthier, Robin, Scott, Helen K., Aggarwal, Varinder K.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 11.04.2011
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
borates
Chemistry
Chemistry, Multidisciplinary
chirality
natural products
olefination
Physical Sciences
Science & Technology
stereogenic centers
CARBON CENTERS
ASYMMETRIC-SYNTHESIS
chirality
borates
ANTAGONIST LY426965
SECONDARY ALCOHOLS
natural products
MARINE ALGA
ALGA SPOROCHNUS-BOLLEANUS
MIGRATORY APTITUDES
FISH DETERRENT
stereogenic centers
olefination
ALLYLIC SUBSTITUTIONS
ALKYL-GROUPS
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Summary:Pin it down: A range of substrates that bear versatile functional groups with quaternary stereogenic centers have been prepared with very high enantioselectivity from tertiary boronic esters (see scheme; Cb=N,N‐diisopropylcarbamoyl, pin=pinacolato). The preparation of allylboronic esters bearing contiguous quaternary and tertiary stereogenic centers, and applications to natural product synthesis are also reported.
Bibliography:European Research Council
ERC - No. FP7/2007-2013; No. 246785
ArticleID:ANIE201008067
istex:F6592C0AA88DF45C3F22FEF35F6B7F9F96BA650D
EPSRC
ark:/67375/WNG-0N25LB3T-7
We thank the EPSRC and the European Research Council (ERC) in the context of the European Community′s Seventh Framework Programme (FP7/2007-2013, ERC grant no. 246785) for financial support. V.K.A. thanks the Royal Society for a Wolfson Research Merit Award and EPSRC for a Senior Research Fellowship. R. L-G. is grateful to the FQRNT for a postdoctoral fellowship. We thank Frontier Scientific for generous donation of boronic acids and boronic esters.
We thank the EPSRC and the European Research Council (ERC) in the context of the European Community′s Seventh Framework Programme (FP7/2007‐2013, ERC grant no. 246785) for financial support. V.K.A. thanks the Royal Society for a Wolfson Research Merit Award and EPSRC for a Senior Research Fellowship. R. L‐G. is grateful to the FQRNT for a postdoctoral fellowship. We thank Frontier Scientific for generous donation of boronic acids and boronic esters.
researchfish
UKRI
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201008067