Cooperative Catalytic Reactions Using Lewis Acids and Organocatalysts: Enantioselective Propargylic Alkylation of Propargylic Alcohols Bearing an Internal Alkyne with Aldehydes

被引：54

作者：

Motoyama, Kazuki ^{[1
]}

Ikeda, Masahiro ^{[1
]}

Miyake, Yoshihiro ^{[1
]}

Nishibayashi, Yoshiaki ^{[1
]}

机构：

[1] Univ Tokyo, Inst Engn Innovat, Sch Engn, Bunkyo Ku, Tokyo 1138656, Japan

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 12期

关键词：

Enantioselectivity; Alkylation; Lewis acids; Organocatalysis; Alkynes; FECL3-CATALYZED NUCLEOPHILIC-SUBSTITUTION; TRANSITION-METAL; BRONSTED ACID; ALPHA-ALKYLATION; AROMATIC-COMPOUNDS; MICHAEL ADDITION; ASYMMETRIC ALKYLATION; ALLYLIC ALKYLATION; RELAY CATALYSIS; ALLENYLIDENE;

D O I：

10.1002/ejoc.201100044

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective propargylic alkylation of propargylic alcohols bearing an internal alkyne moiety with aldehydes in the presence of a metal salt as the Lewis acid and an optically active secondary amine as the co-catalyst has been found to give the corresponding propargylic alkylated products in high yields as a mixture of two diastereoisomers with high enantioselectivity.

引用

页码：2239 / 2246

页数：8

共 8 条

[1] Cooperative Catalytic Reactions Using Organocatalysts and Transition-Metal Catalysts: Enantioselective Propargylic Alkylation of Propargylic Alcohols with Aldehydes
Ikeda, Masahiro
Miyake, Yoshihiro
Nishibayashi, Yoshiaki
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (40) : 7289 - 7293
[2] Cooperative Catalytic Reactions Using Organocatalysts and Transition Metal Catalysts: Enantioselective Propargylic Alkylation of Propargylic Esters with Aldehydes
Yoshida, Akiko
Ikeda, Masahiro
Hattori, Gaku
Miyake, Yoshihiro
Nishibayashi, Yoshiaki
ORGANIC LETTERS, 2011, 13 (04) : 592 - 595
[3] Cooperative Catalytic Reactions Using Organocatalysts and Transition Metal Catalysts: Propargylic Allylation of Propargylic Alcohols with α,β-Unsaturated Aldehydes
Ikeda, Masahiro
Miyake, Yoshihiro
Nishibayashi, Yoshiaki
ORGANOMETALLICS, 2012, 31 (09) : 3810 - 3813
[4] Cooperative Catalysis: Enantioselective Propargylic Alkylation of Propargylic Alcohols with Enecarbamates Using Ruthenium/Phosphoramide Hybrid Catalysts
Senda, Yasushi
Nakajima, Kazunari
Nishibayashi, Yoshiaki
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (13) : 4060 - 4064
[5] Cooperative Catalytic Reactions Using Distinct Transition-Metal Catalysts: Ruthenium- and Copper-Catalyzed Enantioselective Propargylic Alkylation
Ikeda, Masahiro
Miyake, Yoshihiro
Nishibayashi, Yoshiaki
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (11) : 3321 - 3328
[6] Enantioselective catalytic addition of allyl organometallic reagents to aldehydes promoted by [Cr(Salen)]: the hidden role played by weak Lewis acids in metallo-Salen promoted reactions
Bandini, M
Cozzi, PG
Umani-Ronchi, A
TETRAHEDRON, 2001, 57 (05) : 835 - 843
[7] Facile and selective synthesis of propargylic amines and 1,6-diynes:: One-pot three-component coupling reactions of alkynylsilanes, aldehydes and Amines by a cooperative catalytic system comprised of CuCl and Cu(OTf)2
Sakai, Norio
Uchida, Naoki
Konakahara, Takeo
SYNLETT, 2008, (10) : 1515 - 1519
[8] A novel chiral zirconium catalyst for enantioselective aldol and Mannich-type reactions. Catalytic activation of both aldehydes and imines using a similar chiral Lewis acid
Kobayashi, S
Ishitani, H
Yamashita, Y
Ueno, M
Shimizu, H
TETRAHEDRON, 2001, 57 (05) : 861 - 866

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