Pd-Catalyzed Asymmetric Allylic Substitution Cascade of But-2-ene-1,4-diyl Dimethyl Dicarbonate for the Synthesis of Chiral 2,3-Dihydrofurans

被引：23

作者：

Liu, Hao ^{[1
]}

Sun, Zhenliang ^{[2
]}

Xu, Kai ^{[1
]}

Zheng, Yan ^{[1
]}

Liu, Delong ^{[1
]}

Zhang, Wanbin ^{[1
,3
]}

机构：

[1] Shanghai Jiao Tong Univ, Sch Pharm, Shanghai Key Lab Mol Engn Chiral Drugs, Shanghai 200240, Peoples R China

[2] Southern Med Univ, Fengxian Hosp, Shanghai 201499, Peoples R China

[3] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Frontiers Sci Ctr Transformat Mol, Shanghai 200240, Peoples R China

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 12期

基金：

中国国家自然科学基金;

关键词：

ALPHA-AMINO-ACIDS; ENANTIOSELECTIVE SYNTHESIS; DIASTEREODIVERGENT ACCESS; WILSON REARRANGEMENT; 4+1 CYCLOADDITIONS; DUAL CATALYSIS; ALKYLATION; HYDROGENATION; DERIVATIVES; ALLYLATION;

D O I：

10.1021/acs.orglett.0c01483

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein an efficient Pd-catalyzed asymmetric allylic substitution cascade of both (E)- and (Z)-but-2-ene-1,4-diyl dimethyl dicarbonates with alpha-substituted cyano ketones is described for the preparation of chiral 2,3-dihydrofurans in up to 97% yield with 98% ee. A suggested steric control process has been proposed to illustrate the differences in enantioselectivity between the reactions of (E)- and (Z)-allyl substrates. The cascade reaction could be conducted on a gram-scale, and the resulting product allows for several transformations.

引用

页码：4680 / 4685

页数：6

共 50 条

[21] Divergent Asymmetric Synthesis of Chiral Spiroheterocycles through Pd-Catalyzed Enantio- and Diastereoselective [3+2] Spiroannulation
Jeon, Hyun Ji
Park, Su Min
Lee, Yu Lim
Lee, Sang-gi
ORGANIC LETTERS, 2022, 24 (50) : 9189 - 9193
[22] Thieme Chemistry Journals Awardees - Where Are They Now? Chiral Sulfinamide Ligands and Pd-Catalyzed Asymmetric Allylic Alkylations of Ethyl 2-Fluoroacetoacetate
Zhao, Mingzhu
Tian, Yawei
Zhao, Xiaoming
SYNLETT, 2017, 28 (14) : 1801 - 1806
[23] Efficient synthesis of 2,3-dihydrofurans via the highly selective Pd(0)catalyzed coupling-cyclization reaction of 3,4-allenols with aryl iodides
Ma, SM
Gao, WH
SYNLETT, 2002, (01) : 65 - 68
[24] Pd-catalyzed asymmetric allylic alkylation of 2-substituted cycloalkenyl carbonates using a chiral diaminophosphine oxide:: (S,RP)-Ph-DIAPHOX
Jin, Long
Nemoto, Tetsuhiro
Nakamura, Hiroshi
Hamada, Yasumasa
TETRAHEDRON-ASYMMETRY, 2008, 19 (09) : 1106 - 1113
[25] Synthesis of Chiral 2-trifluoromethyl-4-(tetrahydroquinolinyl)-4H-chromenes via Pd-Catalyzed Asymmetric Amination
Wang, Bangzhong
Sun, Luyang
Zhang, Pengyue
Zhang, Shuaibo
Zhao, Jinfeng
Qu, Jingping
Zhou, Yuhan
ADVANCED SYNTHESIS & CATALYSIS, 2025,
[26] Asymmetric Synthesis of 2-Substituted Hexahydroquinolin-4-ones Using a Pd-Catalyzed Asymmetric Allylic Amination and Intramolecular Mannich Reaction: Catalytic Asymmetric Synthesis of 2-epi-cis-195A
Kakugawa, Kazumi
Nemoto, Tetsuhiro
Kohno, Yuta
Hamada, Yasumasa
SYNTHESIS-STUTTGART, 2011, (16): : 2540 - 2548
[27] Novel N,S- and N,Se-planar chiral [2,2]paracyclophane ligands:: synthesis and application in Pd-catalyzed allylic alkylation
Hou, XL
Wu, XW
Dai, LX
Cao, BX
Sun, J
CHEMICAL COMMUNICATIONS, 2000, (13) : 1195 - 1196
[28] Efficient synthesis of 4-(2′-alkenyl)-2,5-dihydrofurans and 5,6-dihydro-2H-pyrans via the Pd-catalyzed cyclizative coupling reaction of 2,3-or 3,4-allenols with allylic halides
Ma, SM
Gao, WZ
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (17): : 6104 - 6112
[29] Asymmetric Synthesis of Bioxindole-Substituted Hexahydrofuro[2,3-b]furans via Hydroquinine Anthraquinone-1,4-diyl Diether-Catalyzed Domino Annulation of Acylidenoxindoles/Isatins, Acylidenoxindoles and Allenoates
Yang, Hai-Bin
Zhao, Yun-Zhou
Sang, Rui
Wei, Yin
Shi, Min
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (18) : 3799 - 3808
[30] Highly Regio- and Enantioselective Synthesis of Polysubstituted 2H-Pyrroles via Pd-Catalyzed Intermolecular Asymmetric Allylic Dearomatization of Pyrroles
Zhuo, Chun-Xiang
Zhou, Yong
You, Shu-Li
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (18) : 6590 - 6593

← 1 2 3 4 5 →