Projects per year
Abstract
Diborylmethane can be homologated uni- and bidirectionally by using enantiomerically pure lithium-stabilized carbenoids to give 1,2- and 1,3-bis(boronic esters), respectively, in good yield and with excellent levels of enantio- and diastereoselectivity. The high sensitivity of the transformation to steric hindrance enables the exclusive operation of either manifold, effected through the judicious choice of the type of carbenoid, which can be a sparteine-ligated or a diamine-free lithiated benzoate/carbamate. The scope of the 1,2-bis(boronic esters) so generated is complementary to that encompassed by the asymmetric diboration of alkenes, in that primary-secondary and primary-tertiary 1,2-bis(boronic esters) can be prepared with equally high levels of selectivity and that functional groups, such as terminal alkynes and alkenes, are tolerated. Methods for forming C2-symmetric and non-symmetrical anti and syn 1,3-bis(boronic esters) are also described and represent a powerful route towards 1,3-functionalized synthetic intermediates.
Original language | English |
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Pages (from-to) | 2898-2903 |
Number of pages | 6 |
Journal | Chemical Science |
Volume | 8 |
Issue number | 4 |
Early online date | 9 Feb 2017 |
DOIs | |
Publication status | Published - 1 Apr 2017 |
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Dive into the research topics of 'Selective uni- and bidirectional homologation of diborylmethane'. Together they form a unique fingerprint.Projects
- 4 Finished
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FRESCO: Efficient, Flexible Synthesis of Molecules with Tailored Shapes: from Photoswitchable Helices to anti-Cancer Compounds
Aggarwal, V. K. (Principal Investigator)
1/10/15 → 31/03/21
Project: Research
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A 13C NMR Coldprobe to Underpin Chemistry Research.
Butts, C. P. (Principal Investigator)
28/02/14 → 29/11/17
Project: Research
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3-month Core Capability for Chemistry Research
Crosby, J. (Principal Investigator)
1/01/13 → 1/04/13
Project: Research