Allenylzinc reagents:: new trends and synthetic applications

被引：34

作者：

Botuha, Candice

Chemla, Fabrice

Ferreira, Franck

Perez-Luna, Alejandro

Roy, Brindaban

机构：

[1] Univ Paris 06, UMR7611, Chim Organ Lab, FR2769, F-75252 Paris 05, France

[2] Univ Kalyani, Dept Chem, Kalyani 741235, W Bengal, India

来源：

NEW JOURNAL OF CHEMISTRY | 2007年 / 31卷 / 09期

关键词：

D O I：

10.1039/b706541h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The last developments in our research efforts involving allenylzinc reagents are summarized. These interesting organometallic compounds allow the stereoselective and enantioselective synthesis of acetylenic epoxides, aziridines and amino alcohols. Some synthetic applications of these highly functionalized substrates are also presented through the synthesis of homopropargylic alcohols and allenic ketones. Further applications in the total synthesis of heterocyclic natural products are also discussed.

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页码：1552 / 1567

页数：16

相关论文

共 202 条

[51] 1,3-DIASTEREOCONTROL WITH BROMOALLENES - SYNTHESIS OF ENANTIOMERICALLY PURE BETA-BRANCHED ALPHA-AMINO-ACIDS [J].

DANIELLO, F ;

MANN, A ;

TADDEI, M ;

WERMUTH, CG .

TETRAHEDRON LETTERS, 1994, 35 (42) :7775-7778

[52] Direct asymmetric synthesis of β-amino ketones from sulfinimines (N-sulfinylimines).: Synthesis of (-)-indolizidine 209B [J].

Davis, FA ;

Yang, B .

ORGANIC LETTERS, 2003, 5 (26) :5011-5014

[53] Improved asymmetric synthesis of aziridine 2-phosphonates using (S)-(+)-2,4,6-trimethylphenylsulfinamide [J].

Davis, FA ;

Ramachandar, T ;

Wu, YZ .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (18) :6894-6898

[54] Sulfinimine-mediated asymmetric synthesis of β-hydroxy α-amino phosphonates [J].

Davis, FA ;

Prasad, KR .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (19) :7249-7253

[55] Asymmetric synthesis of aziridine 2-phosphonates from enantiopure sulfinimines (N-sulfinyl imines).: Synthesis of α-amino phosphonates [J].

Davis, FA ;

Wu, YZ ;

Yan, HX ;

McCoull, W ;

Prasad, KR .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (06) :2410-2419

[56] N-sulfinyl β-amino Weinreb amides:: Synthesis of enantiopure β-amino carbonyl compounds.: Asymmetric synthesis of (+)-sedridine and (-)-allosedridine [J].

Davis, FA ;

Prasad, KR ;

Nolt, MB ;

Wu, YZ .

ORGANIC LETTERS, 2003, 5 (06) :925-927

[57] δ-amino β-keto esters, a designed polyfunctionalized chiral building block for alkaloid synthesis.: Asymmetric synthesis of (R)-(+)-2-phenylpiperidine and (-)-SS20846A [J].

Davis, FA ;

Chao, B ;

Fang, TN ;

Szewczyk, JM .

ORGANIC LETTERS, 2000, 2 (08) :1041-1043

[58] Sulfinimine-mediated asymmetric synthesis of (R)-(4-methoxy-3,5-dihydroxyphenyl)glycine: The central amino acid of vancomycin and related agents [J].

Davis, FA ;

Fanelli, DL .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (06) :1981-1985

[59] Aza-Darzens asymmetric synthesis of N-(p-toluenesulfinyl) aziridine 2-carboxylate esters from sulfinimines (N-sulfinyl imines) [J].

Davis, FA ;

Liu, H ;

Zhou, P ;

Fang, TN ;

Reddy, GV ;

Zhang, YL .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (20) :7559-7567

[60]

Davis FA, 1998, CHEM SOC REV, V27, P13

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