Electrophilic amination of racemic and non-racemic allenyltitaniums.: One-pot synthesis of α-hydrazinoalkynes from propargylic alcohol derivatives

被引:27
作者
An, DK [1 ]
Hirakawa, K [1 ]
Okamoto, S [1 ]
Sato, F [1 ]
机构
[1] Tokyo Inst Technol, Dept Biomol Engn, Midori Ku, Kanagawa 2268501, Japan
关键词
electrophilic amination; alpha-hydrazinoalkynes; titanium and compounds; asymmetric synthesis;
D O I
10.1016/S0040-4039(99)00584-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Successive treatment of propargylic carbonates or phosphates with a Ti(O-i-Pr)(4)/2i-PrMgCl reagent and dialkyl azodicarboxylates gave alpha-hydrazinoalkynes in good yields. The reaction, which proceeded with up to 86% chiral transfer, thus has opened up a new route to optically active alpha-hydrazinoalkynes from the optically active propargylic compounds. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3737 / 3740
页数:4
相关论文
共 14 条
[1]   Synthesis of chiral alkynes having 2H or halogen at the secondary or tertiary propargylic stereogenic center by hydrolysis and halogenolysis of optically active allenyltitaniums having axial chirality [J].
An, DK ;
Okamoto, S ;
Sato, F .
TETRAHEDRON LETTERS, 1998, 39 (25) :4555-4558
[2]   Efficient one-pot synthesis of propargylstannanes from propargylic alcohol derivatives via allenyltitaniums [J].
An, DK ;
Okamoto, S ;
Sato, F .
TETRAHEDRON LETTERS, 1998, 39 (27) :4861-4864
[3]  
ASKANI R, 1991, COMPREHENSIVE ORGANI, V6, P118
[4]   ELECTROPHILIC AMINATION OF CARBANIONS [J].
ERDIK, E ;
AY, M .
CHEMICAL REVIEWS, 1989, 89 (08) :1947-1980
[5]   REGIOCONTROLLED AND STEREOCONTROLLED SYNTHESIS OF ALLENIC AND ACETYLENIC DERIVATIVES - ORGANOTITANIUM AND BORON REAGENTS [J].
FURUTA, K ;
ISHIGURO, M ;
HARUTA, R ;
IKEDA, N ;
YAMAMOTO, H .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1984, 57 (10) :2768-2776
[6]   ASYMMETRIC ELECTROPHILIC AMINATION - SYNTHESIS OF ALPHA-AMINO AND ALPHA-HYDRAZINO ACIDS WITH HIGH OPTICAL PURITY [J].
GENNARI, C ;
COLOMBO, L ;
BERTOLINI, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (20) :6394-6395
[7]  
Greck C, 1997, SYNLETT, P741
[8]   Direct vinylation and ethynylation of nitrones, stereodivergent synthesis of allyl and propargyl amines. [J].
Merino, P ;
Anoro, S ;
Castillo, E ;
Merchan, F ;
Tejero, T .
TETRAHEDRON-ASYMMETRY, 1996, 7 (07) :1887-1890
[9]  
MICHELET V, 1995, SYNTHESIS-STUTTGART, P165
[10]   HIGHLY EFFICIENT SYNTHESIS OF PROPARGYLTITANIUM AND ALLENYLTITANIUM REAGENTS FROM PROPARGYL HALIDES OR PROPARGYL ALCOHOL DERIVATIVES - PRACTICAL SYNTHESIS OF ALLENYL AND HOMOPROPARGYL ALCOHOLS [J].
NAKAGAWA, T ;
KASATKIN, A ;
SATO, F .
TETRAHEDRON LETTERS, 1995, 36 (18) :3207-3210