Gold-Catalyzed Atroposelective Synthesis of 1,1′-Binaphthalene-2,3′-diols

被引：50

作者：

Zhang, Jianwei ^{[1
]}

Simon, Martin ^{[1
]}

Golz, Christopher ^{[1
]}

Alcarazo, Manuel ^{[1
]}

机构：

[1] Georg August Univ Gcttingen, Inst Organ & Biomol Chem, Tammannstr 2, D-37077 Gottingen, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2020年 / 59卷 / 14期

关键词：

gold catalysis; biaryls; cationic ligands; chiral phosphines; enantioselectivity; MONODENTATE PHOSPHORAMIDITE LIGANDS; ALPHA-CATIONIC PHOSPHINES; ENANTIOSELECTIVE SYNTHESIS; ATROPISOMERS; RESOLUTION;

D O I：

10.1002/anie.201915456

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly atroposelective (up to 97 % ee) Au-catalyzed synthesis of 1,1 '-binaphthalene-2,3 '-diols is reported starting from a range of substituted benzyl alkynones. Essential for the achievement of high enantioselectivity during the key assembly of the naphto-3-ol unit is the use of TADDOL-derived alpha-cationic phosphonites as ancillary ligands. Preliminary results demonstrate that the transformation of the obtained binaphthyls into axially chiral monodentate phosphines is possible without degradation of enantiopurity.

引用

页码：5647 / 5650

页数：4

共 50 条

[1] Gold-Catalyzed Atroposelective Synthesis of 1,1’-Binaphthalene-2,3’-diols
Zhang, Jianwei
Simon, Martin
Golz, Christopher
Alcarazo, Manuel
Advanced Materials, 2020, 132 (14) : 5696 - 5699
[2] PREPARATION OF ENANTIOMERICALLY PURE 1,1'-BINAPHTHALENE-2,2'-DIOL AND 1,1'-BINAPHTHALENE-2,2'-DITHIOL
FABBRI, D
DELOGU, G
DELUCCHI, O
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (07): : 1748 - 1750
[3] A CONVENIENT SYNTHESIS OF OPTICALLY PURE DIMETHYL 1,1'-BINAPHTHALENE-2,2'-DICARBOXYLATE FROM 1,1'-BINAPHTHALENE-2,2'-DIOL
OHTA, T
ITO, M
INAGAKI, K
TAKAYA, H
TETRAHEDRON LETTERS, 1993, 34 (10) : 1615 - 1616
[4] (R)-(+)-1,1'-BINAPHTHALENE-2,2'-DIOL - ([1,1'-BINAPHTHALENE]-2,2'-DIOL, (R)-)
TRUESDALE, LK
ORGANIC SYNTHESES, 1989, 67 : 13 - 19
[5] A novel one-pot conversion of 2-naphthols into 1,1'-binaphthalene-2,2'-diols
Holy, P
Belohradsky, M
Zavada, J
SYNTHETIC COMMUNICATIONS, 1996, 26 (13) : 2597 - 2601
[6] A Novel One-Pot Conversion of 2-Naphthols into 1,1'-Binaphthalene-2,2'-diols
Holy, P.
Belohradsky, M.
Zavada, J.
Synthetic Communications, 26 (13):
[7] A WIDELY APPLICABLE METHOD OF RESOLUTION OF BINAPHTHYLS - PREPARATION OF ENANTIOMERICALLY PURE 1,1'-BINAPHTHALENE-2,2'-DIOL, 1,1'-BINAPHTHALENE-2,2'-DITHIOL, 2'-MERCAPTO-1,1'-BINAPHTHALENE-2-OL, AND 1,1'-BINAPHTHALENE-8,8'-DIOL
FABBRI, D
DELOGU, G
DELUCCHI, O
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (20): : 6599 - 6601
[8] 1,1′-binaphthalene-2,2′-diyl hydrogen phosphate
Nayak, Susanta K.
Chandrasekhar, S.
Row, T. N. Guru
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : O256 - U4905
[9] (R)-1,1′-binaphthalene-2,2′-diyl dicinnamate
Weng, Wen
Guo, Hong-Xu
Chen, Zhi-Fen
Wang, Qing-Hua
Yao, Bi-Xia
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : O819 - U1554
[10] Convenient synthesis and efficient resolution of 3,3′-bis(benzyloxy)-1,1′-binaphthalene-2,2′-diol
Tsubaki, K
Morikawa, H
Tanaka, H
Fuji, K
TETRAHEDRON-ASYMMETRY, 2003, 14 (10) : 1393 - 1396

← 1 2 3 4 5 →