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1 article(s) from Cho, Inhee

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

Inhee Cho,
Labros Meimetis,
Lee Belding,
Michael J. Katz,
Travis Dudding and
Robert Britton

Beilstein J. Org. Chem. 2011, 7, 1315–1322, doi:10.3762/bjoc.7.154

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Graphical Abstract

Figure 1: Chiral diols useful for asymmetric synthesis and the tetralithio intermediate 8.

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Scheme 1: Directed ortho,ortho'-dimetalation of (R,R)-hydrobenzoin (3).

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Figure 2: Percentage of (R,R)-hydrobenzoin (3) (○), monodeuterohydrobenzoin (13) (■), and dideuterohydrobenzo...

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Figure 3: Percentage of methylhydrobenzoin (14) (■), and dimethylhydrobenzoin (15) (Δ) as determined by ¹H NM...

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Scheme 2: Formation of the tetralithio intermediate 8 and the X-ray crystal structure of the bis(siloxane) 19....

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Scheme 3: Reaction of the tetralithio intermediate 8 with various electrophiles.

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Scheme 4: Reactions of the diiodohydrobenzoin 12 and X-ray crystal structure of the dihydrosilepin 31.

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Scheme 5: Cross coupling reactions of the bis(benzoxaborol) 20 and a short formal synthesis of (R,R)-Vivol (4...

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Published 22 Sep 2011

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