FACTORS INFLUENCING THE STEREOSELECTIVITY IN THE CYCLOADDITION OF IMINO-DIENOPHILES DERIVED FROM AMINO ETHERS, AMINO-ALCOHOLS, AND AMINO-ACID ESTERS

被引：33

作者：

DEVINE, PN ^{[1
]}

REILLY, M ^{[1
]}

OH, T ^{[1
]}

机构：

[1] SUNY,DEPT CHEM,BINGHAMTON,NY 13902

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 37期

关键词：

D O I：

10.1016/S0040-4039(00)73790-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Imino dienophiles derived from amino ethers, amino alcohols and amino esters undergo Lewis acid promoted cycloaddition with Danishefsky's diene. Cyclic chelation between the imine and oxygen atom increases the stereoselectivity of the reaction.

引用

页码：5827 / 5830

页数：4

共 50 条

[31] Synthesis of glycidyl ethers derived from terpene α-amino oximes and β-substituted alcohols on their basis [J].

Shumilova, T. A. ;

Agafontsev, A. M. ;

Tkachev, A. V. .

RUSSIAN CHEMICAL BULLETIN, 2015, 64 (01) :99-106

[32] CHIRAL AMINO-ALCOHOLS FROM BAKER YEAST REDUCTION OF ALPHA-KETO-ACID DERIVATIVES [J].

PEDROCCHIFANTONI, G ;

REDAELLI, S ;

SERVI, S ;

HOGBERG, HE .

GAZZETTA CHIMICA ITALIANA, 1992, 122 (12) :499-502

[33] Simple Methodology for the Preparation of Amino Alcohols from Amino Acid Esters Using NaBH4-Methanol in THF [J].

Goncalves, R. S. B. ;

Pinheiro, A. C. ;

da Silva, E. T. ;

da Costa, J. C. S. ;

Kaiser, C. R. ;

de Souza, M. V. N. .

SYNTHETIC COMMUNICATIONS, 2011, 41 (09) :1276-1281

[34] Copper(II)-Catalyzed Regioselective Cascade Reaction of β,γ-Alkynyl-α-Imino Esters with α-Amino Acid-Derived Esters [J].

Wang, Guilong ;

Chen, Feiyang ;

Liao, Jianqi ;

Chen, Siru ;

Fu, Bing ;

Huang, Qin ;

Wang, Sasa .

CHEMISTRY-AN ASIAN JOURNAL, 2025,

[35] THE STEREOSELECTIVITY ENHANCEMENT BY METAL-IONS IN CHIRAL MICELLARPROMOTED DEACYLATION OF LONG-CHAIN AMINO-ACID ESTERS [J].

OHKUBO, K ;

MATSUMOTO, N .

JOURNAL OF MOLECULAR CATALYSIS, 1981, 12 (03) :393-396

[36] STEREOSELECTIVITY IN METAL COMPLEX CATALYZED-HYDROLYSIS OF AMINO-ACID ESTERS .2. ROLE OF A CATALYST STRUCTURE [J].

BLACKBURN, JR ;

JONES, MM .

JOURNAL OF INORGANIC & NUCLEAR CHEMISTRY, 1973, 35 (05) :1597-1603

[37] STEREOSELECTIVITY IN METAL-COMPLEX CATALYZED-HYDROLYSIS OF AMINO-ACID ESTERS .4. RATE STUDIES [J].

BLACKBURN, JR ;

JONES, MM .

JOURNAL OF INORGANIC & NUCLEAR CHEMISTRY, 1973, 35 (07) :2421-2432

[38] INVESTIGATION OF THE REACTION BETWEEN AMINO-ACIDS OR AMINO-ACID ESTERS AND 9-FORMYLFLUORENE AND ITS EQUIVALENTS - POSSIBLE UTILITY OF THE DERIVED ENAMINES AS AMINO GROUP PROTECTANTS [J].

CARPINO, LA ;

CHAO, HG ;

TIEN, JH .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (18) :4302-4313

[39] OXIME ESTERS AS ACYLATING AGENTS IN THE AMINOLYSIS REACTION - A SIMPLE AND CHEMOSELECTIVE METHOD FOR THE PREPARATION OF AMIDES FROM AMINO-ALCOHOLS [J].

FERNANDEZ, S ;

MENENDEZ, E ;

GOTOR, V .

SYNTHESIS-STUTTGART, 1991, (09) :713-716

[40] MECHANISTIC EVALUATION OF THE RESOLUTION OF ALPHA-AMINO-ACIDS ON DYNAMIC CHIRAL STATIONARY PHASES DERIVED FROM AMINO-ALCOHOLS BY LIGAND-EXCHANGE CHROMATOGRAPHY [J].

HYUN, MH ;

YANG, DH ;

KIM, HJ ;

RYOO, JJ .

JOURNAL OF CHROMATOGRAPHY A, 1994, 684 (02) :189-200

← 1 2 3 4 5 →