Stereodivergent synthesis of 1,4-bifunctional compounds by regio- and diastereoselective Pd-catalyzed allylic substitution reaction

被引：9

作者：

Maezaki, Naoyoshi ^{[1
]}

Yano, Masahiro ^{[1
]}

Hirose, Yuki ^{[1
]}

Itoh, Yoshikazu ^{[1
]}

Tanaka, Tetsuaki ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan

来源：

TETRAHEDRON | 2006年 / 62卷 / 44期

关键词：

catalytic reaction; 1,4-bifunctional compound; stereoselective reaction; 1,3-asymmetric transfer;

D O I：

10.1016/j.tet.2006.08.057

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly stereoselective synthesis of 1,4-bifunctional compounds was accomplished via 1,2-asymmetric induction to alpha-oxyaldehyde and alpha-oxyketone followed by regio- and diastereoselective Pd-catalyzed allylic substitution reaction. We found that trifluoroacetate is a suitable leaving group for the allylic substitution reaction. Various nucleophiles containing carbon, nitrogen, and sulfur can be applied to the method. Both 1,4-syn- and 1,4-anti-adducts were synthesized with high stereoselectivity by using stereodivergent reduction of the propargyl alcohols followed by allylic substitution reaction. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：10361 / 10378

页数：18

共 50 条

[21] A density functional theory investigation on bis(diethylamino)cyclopropenylidene catalyzed synthesis of 1,4-bifunctional compounds
Shyam, Abhijit
Pradhan, Amit Kumar
Mondal, Paritosh
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2021, 34 (09)
[22] Regiodivergent Synthesis of Spirocyclic Compounds through Pd-Catalyzed Regio- and Enantioselective [3+2] Spiroannulation
Trost, Barry M.
Zuo, Zhijun
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (11) : 5806 - 5810
[23] Pd-Catalyzed Regio- and Stereoselective Addition of Boronic Acids to Silylacetylenes: A Stereodivergent Assembly of β,β-Disubstituted Alkenylsilanes and Alkenyl Halides
Kong, Wei
Che, Chao
Wu, Jialin
Ma, Liai
Zhu, Gangguo
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (12): : 5799 - 5805
[24] Ruthenium-Catalyzed Regio- and Enantioselective Allylic Substitution with Water: Direct Synthesis of Chiral Allylic Alcohols
Kanbayashi, Naoya
Onitsuka, Kiyotaka
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (22) : 5197 - 5199
[25] Pd-Catalyzed Asymmetric Annulative Dearomatization of Phenols for Regio- and Enantioselective Synthesis of Spirocyclohexadienones
Mao, Hui-Lin
Wang, Yu-Xin
Wang, Xue
Wang, Hai-Ying
Hao, Wen-Juan
Jiang, Bo
ORGANIC LETTERS, 2023, 25 (32) : 5963 - 5968
[26] A Versatile Synthesis of Vinyl-Substituted Heterocycles via Regio-and Enantioselective Pd-Catalyzed Tandem Allylic Substitution
Qan, Chao
Tang, Wenjun
ORGANIC LETTERS, 2020, 22 (11) : 4483 - 4488
[27] Synthesis of 1-[bis(trifluoromethyl)phosphine]-1′-oxazolinylferrocene ligands and their application in regio- and enantioselective Pd-catalyzed allylic alkylation of monosubstituted allyl substrates
Lai, Zeng-Wei
Yang, Rong-Fei
Ye, Ke-Yin
Sun, Hongbin
You, Shu-Li
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2014, 10 : 1261 - 1266
[28] Synthesis of chiral 1′-substituted oxazolinylferrocenes as chiral ligands for Pd-catalyzed allylic substitution reactions
Park, J
Quan, Z
Lee, S
Ahn, KH
Cho, CW
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 584 (01) : 140 - 146
[29] Regio- and diastereoselective rhodium-catalyzed allylic substitution with acyclic α-alkoxy-substituted copper(I) enolates: Stereodivergent approach to 2,3,6-trisubstituted dihydropyrans
1600, American Chemical Society, Columbus, United States (126):
[30] Mechanistic Insights into the Pd-Catalyzed Intermolecular Asymmetric Allylic Dearomatization of Multisubstituted Pyrroles: Understanding the Remarkable Regio- and Enantioselectivity
Zheng, Chao
Zhuo, Chun-Xiang
You, Shu-Li
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (46) : 16251 - 16259

← 1 2 3 4 5 →