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Article: Effect of the secondary reduction on the enantioselectivity and function of additives in the chiral oxazaborolidine-catalyzed asymmetric borane reduction of ketones
Title | Effect of the secondary reduction on the enantioselectivity and function of additives in the chiral oxazaborolidine-catalyzed asymmetric borane reduction of ketones |
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Authors | |
Issue Date | 2006 |
Citation | Helvetica Chimica Acta, 2006, v. 89, n. 5, p. 1067-1074 How to Cite? |
Abstract | The secondary reduction in the direct and oxazaborolidine-catalyzed asymmetric borane reduction of ketones was investigated by the use of GC/MS tracing titration and control experiments. The results indicate that the secondary reduction affects the enantioselectivity only in noncoordinated solvents at low temperature and not under the usual catalytic reduction conditions because the intermediate alkoxyborane is unstable and quickly converts to borane and dialkoxyborane. The function of an alcohol additive in the asymmetric borane reduction of ketones is to consume excess borane in the reduction system thus inhibiting noncatalytic reduction, which leads to increased enantioselectivity in the catalytic reduction. © 2006 Verlag Helvetica Chimica Acta AG. |
Persistent Identifier | http://hdl.handle.net/10722/291757 |
ISSN | 2023 Impact Factor: 1.5 2023 SCImago Journal Rankings: 0.557 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Liu, Han | - |
dc.contributor.author | Du, Da Ming | - |
dc.contributor.author | Xu, Jiaxi | - |
dc.date.accessioned | 2020-11-17T14:55:03Z | - |
dc.date.available | 2020-11-17T14:55:03Z | - |
dc.date.issued | 2006 | - |
dc.identifier.citation | Helvetica Chimica Acta, 2006, v. 89, n. 5, p. 1067-1074 | - |
dc.identifier.issn | 0018-019X | - |
dc.identifier.uri | http://hdl.handle.net/10722/291757 | - |
dc.description.abstract | The secondary reduction in the direct and oxazaborolidine-catalyzed asymmetric borane reduction of ketones was investigated by the use of GC/MS tracing titration and control experiments. The results indicate that the secondary reduction affects the enantioselectivity only in noncoordinated solvents at low temperature and not under the usual catalytic reduction conditions because the intermediate alkoxyborane is unstable and quickly converts to borane and dialkoxyborane. The function of an alcohol additive in the asymmetric borane reduction of ketones is to consume excess borane in the reduction system thus inhibiting noncatalytic reduction, which leads to increased enantioselectivity in the catalytic reduction. © 2006 Verlag Helvetica Chimica Acta AG. | - |
dc.language | eng | - |
dc.relation.ispartof | Helvetica Chimica Acta | - |
dc.title | Effect of the secondary reduction on the enantioselectivity and function of additives in the chiral oxazaborolidine-catalyzed asymmetric borane reduction of ketones | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1002/hlca.200690084 | - |
dc.identifier.scopus | eid_2-s2.0-33744950099 | - |
dc.identifier.volume | 89 | - |
dc.identifier.issue | 5 | - |
dc.identifier.spage | 1067 | - |
dc.identifier.epage | 1074 | - |
dc.identifier.isi | WOS:000238040800029 | - |
dc.identifier.issnl | 0018-019X | - |