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

[41] Asymmetric synthesis of 2,3-dihydrofurans and of unsaturated bicyclic tetrahydrofurans through α-elimination and migratory cyclization of silyloxy alkenyl aminosulfoxonium salts.: Generation and intramolecular O,Si-bond insertion of chiral disubstituted β-silyloxy alkylidene carbenes
Gais, HJ
Reddy, LR
Babu, GS
Raabe, G
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (15) : 4859 - 4864
[42] Asymmetric Synthesis of 2,3-Dihydrofurans and of Unsaturated Bicyclic Tetrahydrofurans through α-Elimination and Migratory Cyclization of Silyloxy Alkenyl Aminosulfoxonium Salts. Generation and Intramolecular O, Si-Bond Insertion of Chiral Disubstituted β-Silyloxy AlkyHdene Carbenes
Gais, Hans-Joachim
Reddy, Leleti R.
Babu, Gadamsetti S.
Raabe, Gerhard
Journal of the American Chemical Society, 2004, 126 (15): : 4859 - 4864
[43] Chiral oxalamide phosphine (COAP)-Pd-catalyzed enantioselective cascade formal [4+1] annulation for enantioenriched 2,3-disubstituted indolines and further DFT study on regio- and stereocontrol
Zhou, Sheng-Suo
Shen, Jun-Hao
Liu, Wen-Kai
Sun, Xing-Yun
Song, Jia-Yu
Wang, Zheng
Qi, Zheng-Hang
Wang, Xing-Wang
ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (09) : 2138 - 2146
[44] Asymmetric palladium(0) catalyzed tandem alkylation and SN′ cyclization of 1,4-dichlorobut-2-ene by chiral imines of aminoacetonitrile for the total synthesis of 1-aminocyclopropanecarboxylic acids
Dorizon, P
Su, GF
Ludvig, G
Nikitina, L
Ollivier, J
Salaun, J
SYNLETT, 1998, (05) : 483 - +
[45] Pd-catalyzed asymmetric allylic alkylation of 3-acetoxy-N-(tert-butyloxycarbonyl)-1,2,3,6-tetrahydropyridine -: Preparation of key intermediates for natural product synthesis
Schleich, S
Helmchen, G
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1999, 1999 (10) : 2515 - 2521
[46] Synthesis of diethyl 2-methyl-bicyclo[3.1.1]hept-2-ene-6,6-dicarboxylate by Pd-catalyzed intramolecular allylic alkylation. Stereoselective preparation of its optically homogeneous form from R-(-)-carvone
Galan-Fernandez, Raquel
Clemente-Tejeda, David
del Rio-Nieto, Enrique
Bermejo, Francisco A.
TETRAHEDRON, 2010, 66 (42) : 8247 - 8253
[47] Structurally Divergent Synthesis of Azetidines, 5,6-Dihydro-1,3-oxazines and 2,3-Dihydro-1,4-oxazines through Palladium-Catalyzed Tandem Allylic Substitution Reaction
Meng, Ru-Fang
Kong, Yu-Juan
Wu, Xiao-Yan
Zhang, Huan
Wang, Wei
Liang, Wen-Jie
Zheng, Lan
Lin, Chenxiang
Su, Wei
Xiao, Jun-An
CHINESE JOURNAL OF CHEMISTRY, 2024, 42 (22) : 2773 - 2778
[48] ASYMMETRIC REDUCTION CATALYZED BY TRANSITION-METAL COMPLEXES .4. SYNTHESIS OF CHIRAL AMINES BY MEANS OF RHODIUM COMPLEX AND 2,3-DIHYDROXY BIS(DIPHENYLPHOSPHINO)-1,4-BUTANE(DIOP) OF ISOPROPYLIDENE
KAGAN, HB
LANGLOIS, N
DANG, TP
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 90 (03) : 353 - 365
[49] Pd-Catalyzed asymmetric transformations involving P☆-mono- and P☆,N-bidentate diamidophosphites derived from (2S,3S)-N2,3-dimethyl-N1-phenylpentane-1,2-diamine
Gavrilov, K. N.
Chuchelkin, I. V.
Zheglov, S. V.
Shiryaev, A. A.
Potapova, O. V.
Novikov, I. M.
Rastorguev, E. A.
Petrovskii, P. V.
Davankov, V. A.
RUSSIAN CHEMICAL BULLETIN, 2012, 61 (10) : 1925 - 1932
[50] Pd-Catalyzed asymmetric transformations involving P*-mono- and P*,N-bidentate diamidophosphites derived from (2S,3S)-N2,3-dimethyl-N1-phenylpentane-1,2-diamine
K. N. Gavrilov
I. V. Chuchelkin
S. V. Zheglov
A. A. Shiryaev
O. V. Potapova
I. M. Novikov
E. A. Rastorguev
P. V. Petrovskii
V. A. Davankov
Russian Chemical Bulletin, 2012, 61 : 1925 - 1932

← 1 2 3 4 5 →