A Convenient Synthesis of (S)-H4-BINOL and Its Derivatives via Hydrogenation of Monoesters of BINOL

被引：3

作者：

Li, Xinsheng ^{[1
]}

Ding, Qianchang ^{[1
]}

Ge, Jianfeng ^{[2
]}

Xie, Jianwu ^{[1
]}

Xu, Dongcheng ^{[1
]}

机构：

[1] Zhejiang Normal Univ, Zhejiang Key Lab React Chem Solid Surfaces, Jinhua 321004, Peoples R China

[2] Suzhou Univ, Dept Mat & Engn, Suzhou 215006, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 04期

关键词：

DIELS-ALDER REACTION; ENANTIOSELECTIVE ADDITION; ASYMMETRIC CATALYSIS; AROMATIC-ALDEHYDES; 1,1'-BINAPHTHYLS; REDUCTION; LIGANDS; 5,5',6,6',7,7',8,8'-OCTAHYDRO-1,1'-BI-2-NAPHTHOL; DIETHYLZINC; COMPLEXES;

D O I：

10.1021/jo802542m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new multigram synthesis of chiral (S)-H-4-BINOL and its derivatives in moderate to high yield (up to 83% total yield) via monoesterification of (S)-BINOL, hydrogenation, and saponification reaction was described. The two new monomethylated (S)-H-4-BINOL obtained may be useful materials in asymmetric catalysis.

引用

页码：1785 / 1787

页数：3

共 45 条

[1] Convenient synthesis of chiral H4-BINOL via direct hydrogenation of BINOL
Ding, Qian Chang
Du, Yun Feng
Li, Xin Sheng
Xu, Dong Cheng
CHINESE CHEMICAL LETTERS, 2010, 21 (11) : 1277 - 1280
[2] 3,3′-Anisyl-Substituted BINOL, H4BINOL, and H8BINOL Ligands: Asymmetric Synthesis of Diverse Propargylic Alcohols and Their Ring-Closing Metathesis to Chiral Cycloalkenes
Yue, Yang
Turlington, Mark
Yu, Xiao-Qi
Pu, Lin
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (22): : 8681 - 8689
[3] Synthesis of a Newly Modified Poly-H8-BINOL Ligand and Its Applications in the Asymmetric Addition of Triethylaluminium to Aromatic Aldehydes
Liu Can
Ouyang Kunbing
Yang Nianfa
CHEMICAL RESEARCH IN CHINESE UNIVERSITIES, 2017, 33 (05) : 742 - 745
[4] Synthesis and properties of optically active helical polymers from (S)-3-functional-3′-vinyl-BINOL derivatives
Zhao, Chunhui
Ouyang, Kunbing
Zhang, Jin
Yang, Nianfa
RSC ADVANCES, 2016, 6 (47): : 41103 - 41107
[5] Enantioselective Fluorescent Sensors for Amino Acid Derivatives Based on BINOL Bearing S-tryptophan Unit: Synthesis and Chiral Recognition
Xu, Kuo-Xi
Cheng, Peng-Fei
Zhao, Jin
Wang, Chao-Jie
JOURNAL OF FLUORESCENCE, 2011, 21 (03) : 991 - 1000
[6] Synthesis of Bis-BINOL Derivatives: Linking via the 3-, 4-, or 5-Position by Generation of Suitable C1-Symmetric Precursors
Kohlhaas, Martha
Lutz, Fabian
Paransothy, Nirtharsan
Octa-Smolin, Frescilia
Woelper, Christoph
Niemeyer, Jochen
SYNTHESIS-STUTTGART, 2020, 52 (06): : 853 - 860
[7] Rapid Synthesis of 3,3′ Bis-Arylated BINOL Derivatives Using a C-H Borylation in Situ Suzuki-Miyaura Coupling Sequence
Ahmed, Ijaz
Clark, Daniel A.
ORGANIC LETTERS, 2014, 16 (16) : 4332 - 4335
[8] An Enantioselective Synthesis of an 11-β-HSD-1 Inhibitor via an Asymmetric Methallylation Catalyzed by (S)-3,3′-F2-BINOL
Zhang, Yongda
Wu, Jiang-Ping
Li, Guisheng
Fandrick, Keith R.
Gao, Joe
Tan, Zhulin
Johnson, Joe
Li, Wenjie
Sanyal, Sanjit
Wang, Jun
Sun, Xiufeng
Lorenz, Jon C.
Rodriguez, Sonia
Reeves, Jonathan T.
Grinberg, Nelu
Lee, Heewon
Yee, Nathan
Lu, Bruce Z.
Senanayake, Chris H.
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (06): : 2665 - 2669
[9] BINOL Aza Macrocycle Derivatives: Synthesis of Dinaphthosulfone Aza Macrocycles Using p-Toluenesulfonic Acid (p-TsOH) in Methanol as an Efficient Route and Evaluation of Their 1H NMR Spectra
Rostami, Esmael
Shockravi, Abbas
Fattahi, Hanif
Heydarian, Davood
Minaee, Shima Shahbanzadeh
Naghdi, Shaghayegh
Abouzari-Lotf, Ebrahim
Sadeghpour, Mahdieh
Hosseini, Hamideh
Taheri, Zahra
Ghorbani, Shahla
Javadi, Ali
Ataei, Shahram Mehdipoure
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2009, 184 (08) : 2066 - 2077
[10] Synthesis of a stable adduct of dialane(4) (Al2H4) via hydrogenation of a magnesium(I) dimer
Bonyhady, Simon J.
Collis, David
Frenking, Gernot
Holzmann, Nicole
Jones, Cameron
Stasch, Andreas
NATURE CHEMISTRY, 2010, 2 (10) : 865 - 869

← 1 2 3 4 5 →