Construction of β-haloenamides via direct copper-promoted coupling of lactams with 2-chloro and 2-bromo vinyliodides

被引：52

作者：

Sun, CX ^{[1
]}

Camp, JE ^{[1
]}

Weinreb, SM ^{[1
]}

机构：

[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 09期

关键词：

D O I：

10.1021/ol060093a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cu(I)-catalyzed coupling of lactams with (E)-2-chlorovinyliodides or (E)-2-bromovinyliodides produces the corresponding beta-haloenamides in moderate to excellent yields.

引用

页码：1779 / 1781

页数：3

共 30 条

[11] A stereoselective synthesis of 3-substituted (S)-pyroglutamic and glutamic acids via OBO ester derivatives [J].

Herdeis, C ;

Kelm, B .

TETRAHEDRON, 2003, 59 (02) :217-229

[12] Synthesis of lactams via copper-catalyzed intramolecular vinylation of amides [J].

Hu, TS ;

Li, CZ .

ORGANIC LETTERS, 2005, 7 (10) :2035-2038

[13] Copper-catalyzed coupling of amides and carbamates with vinyl halides [J].

Jiang, L ;

Job, GE ;

Klapars, A ;

Buchwald, SL .

ORGANIC LETTERS, 2003, 5 (20) :3667-3669

[14]

LIN X, 2002, THESIS PENNSYLVANIA

[15] Model studies on total synthesis of the chartellines, spirocyclic β-lactam alkaloids from a marine bryozoan [J].

Lin, XC ;

Weinreb, SM .

TETRAHEDRON LETTERS, 2001, 42 (14) :2631-2633

[16] MARINE ALKALOIDS .14. PROTOTROPY OF CHARTELLINES FROM CHARTELLA-PAPYRACEA [J].

NIELSEN, PH ;

ANTHONI, U ;

CHRISTOPHERSEN, C .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1988, 42 (07) :489-491

[17] Novel synthesis of bromoindolenine with spiro-β-lactam in chartelline [J].

Nishikawa, T ;

Kajii, S ;

Isobe, M .

SYNLETT, 2004, (11) :2025-2027

[18] Synthesis of model compound containing an indole spiro-β-lactam moiety with vinylchloride in chartellines [J].

Nishikawa, T ;

Kajii, S ;

Isobe, M .

CHEMISTRY LETTERS, 2004, 33 (04) :440-441

[19] A new strategy toward indole alkaloids involving an intramolecular cycloaddition/rearrangement cascade [J].

Padwa, A ;

Brodney, MA ;

Lynch, SM ;

Rashatasakhon, P ;

Wang, Q ;

Zhang, HJ .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (11) :3735-3745

[20] CuI/N,N-dimethylglycine-catalyzed coupling of vinyl halides with amides or carbamates [J].

Pan, XH ;

Cai, Q ;

Ma, DW .

ORGANIC LETTERS, 2004, 6 (11) :1809-1812

← 1 2 3 →