Journal
TETRAHEDRON
Volume 62, Issue 15, Pages 3704-3709Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2006.01.060
Keywords
enantioselective reductions; chiral lithium aluminum hydrides; X-ray structure analyses; transition structure analyses
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A series of new chiral lithium aluminium hydrides based on BIFOL (biphenyl-2,2'-bisfenchol) and various alkyl alcohols (i.e., methanol, n-butanol, tert-butanol yielding BIFAl-H's) was synthesized and characterized by single crystal X-ray analyses. These investigations point to alkoxide redistribution for BIFAI-H-(O-tBu) (biphenyl-2,2-bisfenchol aluminum hydride) species. The new BIFAI-H reaaents are suitable to reduce aryl alkyl ketones with up to 62% ee. Computational transition structure analyses help to explain the experimentally observed enantioselectivities. (c) 2006 Elsevier Ltd. All rights reserved.
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