Directed ortho,ortho'-dimetalation of hydrobenzoin: Rapid access to hydrobenzoin derivatives useful for asymmetric synthesis

A variety of ortho,ortho'-disubstituted hydrobenzoin derivatives are readily accessible through a directed ortho,ortho'-dimetalation strategy in which the alcohol functions in hydrobenzoin are deprotonated by n-BuLi and the resulting lithium benzyl alkoxides serve as directed metalation gr...

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Main Authors:	Inhee Cho, Labros Meimetis, Lee Belding, Michael J. Katz, Travis Dudding, Robert Britton
Format:	Article
Language:	English
Published:	Beilstein-Institut 2011-09-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	chiral diol directed ortho-metalation hydrobenzoin
Online Access:	https://doi.org/10.3762/bjoc.7.154

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spelling	doaj-2fcc17de538c4fc4969dc44441b39d1f2021-02-02T05:07:26ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972011-09-01711315132210.3762/bjoc.7.1541860-5397-7-154Directed ortho,ortho'-dimetalation of hydrobenzoin: Rapid access to hydrobenzoin derivatives useful for asymmetric synthesisInhee Cho0Labros Meimetis1Lee Belding2Michael J. Katz3Travis Dudding4Robert Britton5Department of Chemistry, Simon Fraser University, 8888 University Drive, Burnaby, B.C., Canada, V5S 1S6Department of Chemistry, Simon Fraser University, 8888 University Drive, Burnaby, B.C., Canada, V5S 1S6Department of Chemistry, Simon Fraser University, 8888 University Drive, Burnaby, B.C., Canada, V5S 1S6Department of Chemistry, Simon Fraser University, 8888 University Drive, Burnaby, B.C., Canada, V5S 1S6Department of Chemistry, Brock University, 500 Glenridge Ave, St Catharines, ON, Canada, L2S 3A1Department of Chemistry, Simon Fraser University, 8888 University Drive, Burnaby, B.C., Canada, V5S 1S6A variety of ortho,ortho'-disubstituted hydrobenzoin derivatives are readily accessible through a directed ortho,ortho'-dimetalation strategy in which the alcohol functions in hydrobenzoin are deprotonated by n-BuLi and the resulting lithium benzyl alkoxides serve as directed metalation groups. The optimization and scope of this reaction are discussed, and the utility of this process is demonstrated in the one-pot preparation of a number of chiral diols as well as a short synthesis of the chiral ligand Vivol.https://doi.org/10.3762/bjoc.7.154chiral dioldirected ortho-metalationhydrobenzoin
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Inhee Cho Labros Meimetis Lee Belding Michael J. Katz Travis Dudding Robert Britton
spellingShingle	Inhee Cho Labros Meimetis Lee Belding Michael J. Katz Travis Dudding Robert Britton Directed ortho,ortho'-dimetalation of hydrobenzoin: Rapid access to hydrobenzoin derivatives useful for asymmetric synthesis Beilstein Journal of Organic Chemistry chiral diol directed ortho-metalation hydrobenzoin
author_facet	Inhee Cho Labros Meimetis Lee Belding Michael J. Katz Travis Dudding Robert Britton
author_sort	Inhee Cho
title	Directed ortho,ortho'-dimetalation of hydrobenzoin: Rapid access to hydrobenzoin derivatives useful for asymmetric synthesis
title_short	Directed ortho,ortho'-dimetalation of hydrobenzoin: Rapid access to hydrobenzoin derivatives useful for asymmetric synthesis
title_full	Directed ortho,ortho'-dimetalation of hydrobenzoin: Rapid access to hydrobenzoin derivatives useful for asymmetric synthesis
title_fullStr	Directed ortho,ortho'-dimetalation of hydrobenzoin: Rapid access to hydrobenzoin derivatives useful for asymmetric synthesis
title_full_unstemmed	Directed ortho,ortho'-dimetalation of hydrobenzoin: Rapid access to hydrobenzoin derivatives useful for asymmetric synthesis
title_sort	directed ortho,ortho'-dimetalation of hydrobenzoin: rapid access to hydrobenzoin derivatives useful for asymmetric synthesis
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2011-09-01
description	A variety of ortho,ortho'-disubstituted hydrobenzoin derivatives are readily accessible through a directed ortho,ortho'-dimetalation strategy in which the alcohol functions in hydrobenzoin are deprotonated by n-BuLi and the resulting lithium benzyl alkoxides serve as directed metalation groups. The optimization and scope of this reaction are discussed, and the utility of this process is demonstrated in the one-pot preparation of a number of chiral diols as well as a short synthesis of the chiral ligand Vivol.
topic	chiral diol directed ortho-metalation hydrobenzoin
url	https://doi.org/10.3762/bjoc.7.154
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Directed ortho,ortho'-dimetalation of hydrobenzoin: Rapid access to hydrobenzoin derivatives useful for asymmetric synthesis

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