Enantioselective Synthesis of 2-Methyl-1,2-syn- and 2-Methyl-1,2-anti-3-butenediols via Allene Hydroboration−Aldehyde Allylboration Reaction Sequences
- 24 September 2009
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 131 (41), 14602-14603
- https://doi.org/10.1021/ja904599h
Abstract
The hydroboration of allene 7 with (dIpc)2BH at 0 °C provides the kinetic allylborane 12Z with >20:1 selectivity. However, when the hydroboration is performed at 85 °C, the kinetically formed allylborane isomerizes to give the thermodynamic allylborane 12E with ≥12:1 selectivity. Subsequent treatment of 12Z or 12E with aldehydes at −78 °C, followed by oxidative workup, provides the 2-methyl-1,2-diols 8 and 9 in good yield and with 80−92% e.e.Keywords
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