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Synthesis 2006(1): 24-30
DOI: 10.1055/s-2005-921756
DOI: 10.1055/s-2005-921756
PAPER
© Georg Thieme Verlag Stuttgart · New York
New Enantiomerically Pure Allylboronic Esters in Allyl Additions: Synthesis and NMR Investigation of Intermediates
Further Information
Publication History
Received
31 October 2005
Publication Date:
16 December 2005 (online)


Abstract
Enantiomerically pure allylboronic esters 1 + 2 with a stereogenic center α to the boron moiety can be obtained by a sigmatropic rearrangement of boron containing allyl alcohols. Allyl additions with the new reagents are highly selective, which was shown via the direct measurement of the diastereoisomeric ratio of the intermediates 5 + 6 by characteristic NMR chemical shifts. The observations are not limited to ester containing reagents, but holds also true for hydrocarbon side-chains (e.g. in 11 + 12) that were readily obtained by reducing the ester.
Key words
spectroscopy - allylations - boron - stereoselectivity