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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收藏

页码：1552 / 1567

页数：16

相关论文

共 202 条

[1] 1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis [J].

Ager, DJ ;

Prakash, I ;

Schaad, DR .

CHEMICAL REVIEWS, 1996, 96 (02) :835-875

[2] DETERMINATION OF ABSOLUTE STRUCTURE OF (-)-OUDEMANSIN-B [J].

AKITA, H ;

MATSUKURA, H ;

OISHI, T .

TETRAHEDRON LETTERS, 1986, 27 (44) :5397-5400

[3] A versatile approach to N-Boc-statine and N-Boc-norstatine based on the reduction of 1-trialkylsilyl acetylenic ketones.: Strong remote effect of the C(1) substituent on the stereoselectivity [J].

Alemany, C ;

Bach, J ;

Farràs, J ;

Garcia, J .

ORGANIC LETTERS, 1999, 1 (11) :1831-1834

[4] REACTIVE INTERMEDIATES .22. FORMATION OF 2H-AZIRINES BY OXIDATION OF N-AMINOPHTHALIMIDE IN PRESENCE OF ALKYNES [J].

ANDERSON, DJ ;

GILCHRIST, TL ;

GYMER, GE ;

REES, CW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (06) :550-555

[5] Diastereoselective syntheses of 2-amino propargyl alcohols.: Chiral building blocks for enantiopure amino γ-lactones and 5-hydroxy-piperidinone derivatives [J].

Andres, Jose Maria ;

Pedrosa, Rafael ;

Perez-Encabo, Alfonso .

TETRAHEDRON LETTERS, 2006, 47 (30) :5317-5320

[6]

[Anonymous], CHEM ORGANOLITHIUM C, DOI DOI 10.1002/047002111X.CH18

[7] AMASTATIN, AN INHIBITOR OF AMINOPEPTIDASE-A, PRODUCED BY ACTINOMYCETES [J].

AOYAGI, T ;

TOBE, H ;

KOJIMA, F ;

HAMADA, M ;

TAKEUCHI, T ;

UMEZAWA, H .

JOURNAL OF ANTIBIOTICS, 1978, 31 (06) :636-638

[8] DAUNOMYCIN .I. STRUCTURE OF DAUNOMYCINONE [J].

ARCAMONE, F ;

BARBIERI, W ;

FRANCESC.G ;

MONDELLI, R ;

OREZZI, P ;

CASSINELLI, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (23) :5334-&

[9] PREPARATION OF A CHIRAL LACTONE FROM LAEVOGLUCOSAN - A KEY INTERMEDIATE FOR SYNTHESIS OF THE SPIROACETAL MOIETIES OF THE AVERMECTINS AND MILBEMYCINS [J].

BAKER, R ;

BOYES, RHO ;

BROOM, DMP ;

OMAHONY, MJ ;

SWAIN, CJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (07) :1613-1621

[10] CONSTRUCTION OF TRANS-FUSED POLYCYCLIC ETHERS - METHODOLOGY FOR THE BREVETOXINS [J].

BARTLETT, PA ;

TING, PC .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (12) :2230-2240

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