SYNTHESIS OF ALPHA,ALPHA-DISUBSTITUTED ACETIC-ACIDS USING LOW-VALENT TITANIUM

被引:19
作者
GARCIA, M [1 ]
DELCAMPO, C [1 ]
LLAMA, EF [1 ]
SINISTERRA, JV [1 ]
机构
[1] UNIV COMPLUTENSE MADRID, FAC PHARM, DEPT ORGAN & PHARMACEUT CHEM, E-28040 MADRID, SPAIN
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1995年 / 13期
关键词
D O I
10.1039/p19950001771
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Dihalogenocarbenes generated using low-valent titanium (LVT) undergo a one-pot cycloaddition to diaryl, aryl alkyl or dialkyl ketones to give alpha,alpha-disubstituted acetic acids such as (R,S)-2-arylpropanoic acids. TiI4 proved most effective in this reaction for which the product yield was optimized by use of an excess of reducing agent.
引用
收藏
页码:1771 / 1773
页数:3
相关论文
共 47 条
[1]   FORMATION OF CARBENES FROM HALO CARBON RADICALS [J].
ASHBY, EC ;
DESHPANDE, AK ;
DOCTOROVICH, F .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (16) :4205-4206
[3]   PURE ENANTIOMERS OF 2-ARYLPROPIONIC ACIDS - TOOLS IN PAIN RESEARCH AND IMPROVED DRUGS IN RHEUMATOLOGY [J].
BRUNE, K ;
GEISSLINGER, G ;
MENZELSOGLOWEK, S .
JOURNAL OF CLINICAL PHARMACOLOGY, 1992, 32 (10) :944-952
[4]  
COMETTI G, 1982, J ORGANOMET CHEM, V31, P236
[5]   ON THE MECHANISM OF THE TITANIUM-INDUCED REDUCTIVE COUPLING OF KETONES TO OLEFINS [J].
DAMS, R ;
MALINOWSKI, M ;
WESTDORP, I ;
GEISE, HY .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (02) :248-259
[6]   LOW-VALENT ORGANOTITANIUM SPECIES AND THEIR APPLICATIONS TO ORGANIC-SYNTHESIS [J].
DANG, Y ;
GEISE, HJ .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1991, 405 (01) :1-39
[7]  
DOBIER WR, 1988, TETRAHEDRON LETT, V29, P6749
[8]   CATALYTIC METHODS FOR METAL CARBENE TRANSFORMATIONS [J].
DOYLE, MP .
CHEMICAL REVIEWS, 1986, 86 (05) :919-939
[9]  
EYRE, 1965, DICT ORGANIC COMPOUN
[10]  
FADEL A, 1982, SYNLETT, P42