Gold-Catalyzed Hydrosilyloxylation Driving Tandem Aldol and Mannich Reactions

被引：22

作者：

Kang, Dongjin ^{[1
]}

Park, Sangjune ^{[1
]}

Ryu, Taekyu ^{[1
]}

Lee, Phil Ho ^{[1
]}

机构：

[1] Kangwon Natl Univ, Dept Chem, Chunchon 200701, South Korea

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 15期

基金：

新加坡国家研究基金会;

关键词：

ALLYLIC ALCOHOLS; ASYMMETRIC ALDOL; ISOMERIZATION; CONDENSATION; PLATINUM; ALKYNES; CYCLOADDITION; HETEROCYCLES; CARBOCYCLES; DERIVATIVES;

D O I：

10.1021/ol301660f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chemoselective formation of an enolate from alkyne in the presence of a carbonyl and imine group was realized, which constructed a variety of structural motifs under exceedingly mild reaction conditions in a tandem process. Reaction driving tandem hydrosilyloxylation/aldol reactions was achieved through the formation of enol silyl ethers catalytically generated in situ from readily available alkynes. These reactions were expanded to obtain beta-amino enol silyl ethers in good yields via the tandem hydrosilyloxylation/isomerization/Mannich reaction.

引用

页码：3912 / 3915

页数：4

共 71 条

[1] Rhodium-Catalysed Coupling of Allylic, Homoallylic, and Bishomoallylic Alcohols with Aldehydes and N-Tosylimines: Insights into the Mechanism [J].

Ahlsten, Nanna ;

Martin-Matute, Belen .

ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (16) :2657-2666

[2] Two birds with one metallic stone: Single-pot catalysis of fundamentally different transformations [J].

Ajamian, A ;

Gleason, JL .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (29) :3754-3760

[3]

Alcaide B, 2002, EUR J ORG CHEM, V2002, P1595

[4]

Arend M, 1998, ANGEW CHEM INT EDIT, V37, P1044, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO

[5]

2-E

[6] Efficient Synthesis of β-Hydroxy Ketones from Allylic Alcohols by Catalytic Formation of Ruthenium Enolates [J].

Bartoszewicz, Agnieszka ;

Livendahl, Madeleine ;

Martin-Matute, Belen .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (34) :10547-10550

[7] REGIO-SELECTIVE, DIASTEREO-SELECTIVE, AND ENANTIO-SELECTIVE CONDENSATION OF CHIRAL VINYLIC BORATES WITH ALDEHYDES [J].

BASILE, T ;

BIONDI, S ;

BOLDRINI, GP ;

TAGLIAVINI, E ;

TROMBINI, C ;

UMANIRONCHI, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (05) :1025-1029

[8] ASYMMETRIC ALDOL REACTIONS USING (4R-TRANS)-2-(1-METHYL-ETHENYL)-1,3,2-DIOXABOROLANE-4,5-DICARBOXYLIC ACID, BIS-ETHYL ESTER, A CHIRAL PRECURSOR OF THE ACETONE ENOLATE [J].

BOLDRINI, GP ;

LODI, L ;

TAGLIAVINI, E ;

TROMBINI, C ;

UMANIRONCHI, A .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1987, 336 (1-2) :23-28

[9] STEREOSELECTIVE ALDOL REACTIONS WITH ALPHA-UNSUBSTITUTED CHIRAL ENOLATES [J].

BRAUN, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (01) :24-37

[10] Silylene transfer to carbonyl compounds and subsequent Ireland-Claisen rearrangements to control formation of quaternary carbon stereocenters [J].

Calad, SA ;

Woerpel, KA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (07) :2046-2047

← 1 2 3 4 5 6 7 8 →