Silicon-Directed Rhenium-Catalyzed Allylic Carbaminations and Oxidative Fragmentations of γ-Silyl Allylic Alcohols

被引：12

作者：

Chavhan, Sanjay W. ^{[1
]}

Cook, Matthew J. ^{[1
]}

机构：

[1] Queens Univ Belfast, Sch Chem & Chem Engn, Belfast BT9 5AG, Antrim, North Ireland

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2014年 / 20卷 / 17期

关键词：

allylic substitution; carbamination; Hiyama coupling; rhenium; silicon; ELECTRON-DEFICIENT AMINES; ENANTIOSELECTIVE REDUCTION; PROPARGYLIC ALCOHOLS; AMINATION; ISOMERIZATION; SUBSTITUTION; IMINES; REARRANGEMENT; VERSATILE; ALLYLATION;

D O I：

10.1002/chem.201400104

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly regioselective allylic substitution of -silyl allylic alcohols has been achieved that provides the branched isomer as a single product. This high level of regiocontrol is achieved through the use of a vinyl silane group that can perform a Hiyama coupling providing 1,3-disubstituted allylic amines. An unusual oxidative fragmentation product was also observed at elevated temperature that appears to proceed by a Fleming-Tamao-type oxidation-elimination pathway.

引用

页码：4891 / 4895

页数：5

共 70 条

[1]

[Anonymous], 1997, ANGEW CHEM INT ED EN, V36, P976

[2]

[Anonymous], 1968, ANGEW CHEM INT ED EN, V7, P295

[3]

[Anonymous], 2012, ANGEW CHEM INT ED, V51, P3470

[4]

[Anonymous], 2009, ANGEW CHEM INT ED, V48, P4426

[5]

BAILEY N, 1960, J CHEM SOC, V290

[6]

Bartels B., 2002, EUR J INORG CHEM, P2569

[7] Allylic Substitutions Catalyzed by Miscellaneous Metals [J].

Begouin, Jeanne-Marie ;

Klein, Johannes E. M. N. ;

Weickmann, Daniel ;

Plietker, Bernd .

TRANSITION METAL CATALYZED ENANTIOSELECTIVE ALLYLIC SUBSTITUTION IN ORGANIC SYNTHESIS, 2012, 38 :269-320

[8] Molybdenum-catalyzed asymmetric allylic alkylations [J].

Belda, O ;

Moberg, C .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (03) :159-167

[9] Isomerization of allylic silyl ethers catalyzed by ReO3(OSiR3) complexes [J].

Bellemin-Laponnaz, S ;

Le Ny, JP ;

Osborn, JA .

TETRAHEDRON LETTERS, 2000, 41 (10) :1549-1552

[10]

Bellemin-Laponnaz S., 1997, ANGEW CHEM, V109, P1011

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