Highly diastereoselective addition of the lithium enolate of α-diazoacetoacetate to N-sulfinyl imines:: Enantioselective synthesis of 2-oxo and 3-oxo pyrrolidines

被引：36

作者：

Dong, Changqing ^{[1
,2
]}

Mo, Fanyang ^{[1
,2
]}

Wang, Jianbo ^{[1
,2
]}

机构：

[1] Peking Univ, Coll Chem, Minist Educ, BNLMS, Beijing 100871, Peoples R China

[2] Peking Univ, Coll Chem, Minist Educ, Key Lab Bioorgan Chem & Mol Engn, Beijing 100871, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 05期

关键词：

D O I：

10.1021/jo702275a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The highly enantioselective synthesis of 2-oxo and 3-oxo pyrrolidines has been achieved by diastereoselective addition of the lithium enolate of alpha-diazoacetoacetate to chiral N-sulfinyl imines, followed by photoinduced Wolff rearrangement or Rh(II)-catalyzed intramolecular N-H insertion.

引用

页码：1971 / 1974

页数：4

共 62 条

[1] Organocatalytic ring expansion of β-lactams to γ-lactams through a novel N1-C4 bond cleavage.: Direct svnthesis of enantiopure succinimide derivatives [J].

Alcaide, B ;

Almendros, P ;

Cabrero, G ;

Ruiz, MP .

ORGANIC LETTERS, 2005, 7 (18) :3981-3984

[2] Synthesis of optically pure highly functionalized γ-lactams via 2-azetidinone-tethered iminophosphoranes [J].

Alcaide, B ;

Almendros, P ;

Alonso, JM .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (03) :993-996

[3]

[Anonymous], 2005, SCI SYNTH

[4] Intramolecular cyclization of acyl radicals onto the azido group: A new radical approach to cyclized lactams [J].

Benati, L ;

Leardini, R ;

Minozzi, M ;

Nanni, D ;

Spagnolo, P ;

Strazzari, S ;

Zanardi, G .

ORGANIC LETTERS, 2002, 4 (18) :3079-3081

[5] Radical carbonylation/reductive cyclization for the construction of tetrahydrofuran-3-ones and pyrrolidin-3-ones [J].

Berlin, S ;

Ericsson, C ;

Engman, L .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (22) :8386-8396

[6] Aldol-cyclization reaction sequence for the synthesis of tetrahydrofurans [J].

Calter, MA ;

Sugathapala, PM ;

Zhu, C .

TETRAHEDRON LETTERS, 1997, 38 (22) :3837-3840

[7] De novo syntheses of racemic deoxy-C-nucleosides [J].

Calter, MA ;

Zhu, C .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (04) :1415-1419

[8] Ruthenium-catalyzed stereoselective intramolecular carbenoid C-H insertion for β- and γ-lactam formations by decomposition of α-diazoacetamides [J].

Choi, MKW ;

Yu, WY ;

Che, CM .

ORGANIC LETTERS, 2005, 7 (06) :1081-1084

[9] INTRAMOLECULAR GENERATION AND REARRANGEMENT OF AMMONIUM YLIDES FROM COPPER CARBENOIDS - A GENERAL-METHOD FOR THE SYNTHESIS OF CYCLIC AMINES [J].

CLARK, JS ;

HODGSON, PB .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (23) :2701-2702

[10]

Corey EJ, 1999, CHEM PHARM BULL, V47, P1

← 1 2 3 4 5 6 7 →