Synthesis of 2-Hydroxy-8'-(hydroxymethyl)-1,1'-binaphthalene (iso-Homo-BINOL). A New Structural Pattern in the Binaphthyl Realm

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Title:Synthesis of 2-Hydroxy-8'-(hydroxymethyl)-1,1'-binaphthalene (iso-Homo-BINOL). A New Structural Pattern in the Binaphthyl Realm
Creators:
Vyskočil, Štěpán
Lockhart, Stephen C.
Mitchell, William L.
Kočovský, Pavel
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 68, 5, pp. 907-916
Uncontrolled Keywords:Biaryls, NOBIN, Binaphthyls, Suzuki-Miyaura cross-coupling, Phenols, Asymmetric reductions, Alcohols, Axially chiral ligands

Abstract

The title compound <strong>7</strong> has been synthesized in a racemic form, using Suzuki coupling (<strong>8</strong> + <strong>15</strong> → <strong>16</strong>) as the key step. Pure enantiomer (<i>S</i>)-(-)-<strong>7</strong> has been obtained by carbonylation of the known bromide (<i>S</i>)-(+)-<strong>12</strong> followed by reduction of the resulting methyl ester (<i>S</i>)-(+)-<strong>18</strong> with LiAlH<sub>4</sub>. <p>

Title:Synthesis of 2-Hydroxy-8'-(hydroxymethyl)-1,1'-binaphthalene (iso-Homo-BINOL). A New Structural Pattern in the Binaphthyl Realm
Creators:
Vyskočil, Štěpán
Lockhart, Stephen C.
Mitchell, William L.
Kočovský, Pavel
Uncontrolled Keywords:Biaryls, NOBIN, Binaphthyls, Suzuki-Miyaura cross-coupling, Phenols, Asymmetric reductions, Alcohols, Axially chiral ligands
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:68
Number:5
Page Range:pp. 907-916
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20030907UNSPECIFIED
ID Code:2093
Item Type:Article
Deposited On:06 Feb 2009 17:15
Last Modified:06 Feb 2009 16:15

Citation

Vyskočil, Štěpán; Lockhart, Stephen C.; Mitchell, William L.; Kočovský, Pavel (2003) Synthesis of 2-Hydroxy-8'-(hydroxymethyl)-1,1'-binaphthalene (iso-Homo-BINOL). A New Structural Pattern in the Binaphthyl Realm. Collection of Czechoslovak Chemical Communications, 68 (5). pp. 907-916. ISSN 0010-0765

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