Direct Chemoselective Allylation of Inert Amide Carbonyls

被引：96

作者：

Oda, Yukiko ^{[1
]}

Sato, Takaaki ^{[1
]}

Chida, Noritaka ^{[1
]}

机构：

[1] Keio Univ, Fac Sci & Technol, Dept Appl Chem, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 03期

关键词：

REDUCTIVE ALKYLATION; VERSATILE CONVERSION; GRIGNARD-REAGENTS; BOND FORMATION; TERTIARY; HYDROZIRCONATION; ORGANOLITHIUM; ENTRY; (+/-)-KOPSIDASINE; LACTAMS/AMIDES;

D O I：

10.1021/ol3000316

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Direct allylation of inert amide carbonyls utilizing the Schwartz reagent afforded either substituted tertiary or secondary amines. A preactivation step was successfully avoided, which is generally a requisite to increase the electrophilicity of amides. The reaction exhibited remarkable functional group tolerance and proceeded even in the presence of methyl esters and nitro groups.

引用

页码：950 / 953

页数：4

共 43 条

[1]

Albericio F, 2001, ORG PREP PROCED INT, V33, P205

[2] Rapid Assembly of Quinolizidines via Consecutive Nucleophilic Cyclizations onto Activated Amides [J].

Belanger, Guillaume ;

O'Brien, Gary ;

Larouche-Gauthier, Robin .

ORGANIC LETTERS, 2011, 13 (16) :4268-4271

[3] Organocerium reactions of benzamides and thiobenzamides: A direct synthesis of tertiary carbinamines [J].

Calderwood, DJ ;

Davies, RV ;

Rafferty, P ;

Twigger, HL ;

Whelan, HM .

TETRAHEDRON LETTERS, 1997, 38 (07) :1241-1244

[4] The preparation and intra- and intermolecular addition reactions of acyclic N-acylimines:: Application to the synthesis of (±)-sertraline [J].

DeNinno, MP ;

Eller, C ;

Etienne, JB .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (21) :6988-6993

[5] Efficient generation and intramolecular cyclization reactions of acyl imines [J].

DeNinno, MP ;

Eller, C .

TETRAHEDRON LETTERS, 1997, 38 (37) :6545-6548

[6]

Denton SM, 1999, SYNLETT, P55

[7] Recent development of peptide coupling reagents in organic synthesis [J].

Han, SY ;

Kim, YA .

TETRAHEDRON, 2004, 60 (11) :2447-2467

[8] HYDROZIRCONATION ORGANIC SYNTHESIS VIA ORGANOZIRCONIUM INTERMEDIATES - SYNTHESIS AND REARRANGEMENT OF ALKYLZIRCONIUM(IV) COMPLEXES AND THEIR REACTION WITH ELECTROPHILES [J].

HART, DW ;

SCHWARTZ, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (26) :8115-8116

[9]

Hoveyda AH, 1996, ANGEW CHEM INT EDIT, V35, P1263

[10] Chemical synthesis of natural product peptides: Coupling methods for the incorporation of noncoded amino acids into peptides [J].

Humphrey, JM ;

Chamberlin, AR .

CHEMICAL REVIEWS, 1997, 97 (06) :2243-2266

← 1 2 3 4 5 →