Unusual reaction of β-hydroxy α-diazo carbonyl compounds with Cl3CCN/NaH and Rh(II)-catalyzed reaction of β-trichloroacetylamino α-diazo carbonyl compounds

被引:31
作者
Shi, WF
Jiang, N
Zhang, SW
Wu, WM
Du, DM
Wang, JB [1 ]
机构
[1] Peking Univ, Coll Chem, Minist Educ,Dept Chem Biol, Key Lab Bioorgan Chem & Mol Engn, Beijing 100871, Peoples R China
[2] San Francisco State Univ, Dept Chem & Biochem, San Francisco, CA 94132 USA
关键词
D O I
10.1021/ol034550o
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The hydroxyl group was directly converted into the trichloroacetylamino group by reacting beta-hydroxy alpha-diazo carbonyl compounds with Cl3CCN and NaH. Rh(II)-catalyzed reactions of the beta-amino alpha-diazo carbonyl compounds were discussed.
引用
收藏
页码:2243 / 2246
页数:4
相关论文
共 15 条
[1]   DETERMINATIONS OF TRANSITION-STATE GEOMETRIES BY THE ENDOCYCLIC RESTRICTION TEST - MECHANISMS OF SUBSTITUTION AT NONSTEREOGENIC ATOMS [J].
BEAK, P .
ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (05) :215-222
[2]   A general, highly enantioselective method for the synthesis of D and L α-amino acids and allylic amines [J].
Chen, YK ;
Lurain, AE ;
Walsh, PJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (41) :12225-12231
[3]  
Doyle M. P., 1998, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides
[4]   SHIKIMATE DERIVED METABOLITES .8. CATALYZED INSERTION REACTIONS OF SUBSTITUTED ALPHA-DIAZOESTERS - A NEW SYNTHESIS OF CIS-ENOATES [J].
IKOTA, N ;
TAKAMURA, N ;
YOUNG, SD ;
GANEM, B .
TETRAHEDRON LETTERS, 1981, 22 (42) :4163-4166
[5]   Investigation of the transition-metal- and acid-catalyzed reactions of β-(N-tosyl)amino diazo carbonyl compounds [J].
Jiang, N ;
Ma, ZH ;
Qu, ZH ;
Xing, XY ;
Xie, LF ;
Wang, JB .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (03) :893-900
[6]   DBU-promoted condensation of acyldiazomethanes to aldehydes and imines under catalytic conditions [J].
Jiang, N ;
Wang, JB .
TETRAHEDRON LETTERS, 2002, 43 (07) :1285-1287
[7]   Lewis acid-catalyzed reactions of ethyl diazoacetate with aldehydes.: Synthesis of α-formyl esters by a sequence of aldol reaction and 1,2-nucleophilic rearrangement [J].
Kanemasa, S ;
Kanai, T ;
Araki, T ;
Wada, E .
TETRAHEDRON LETTERS, 1999, 40 (27) :5055-5058
[8]   Condensation of D-mannosaldehyde derivatives with ethyl diazoacetate. An easy and stereoselective chain elongation methodology for carbohydrates: Application to new syntheses for KDO and 2-deoxy-beta-KDO. [J].
LopezHerrera, FJ ;
SarabiaGarcia, F .
TETRAHEDRON, 1997, 53 (09) :3325-3346
[9]  
LOWRY TH, 1987, MECHANISM THEORY ORG, P342
[10]   ALLYLIC AND PROPARGYLIC IMIDIC ESTERS IN ORGANIC-SYNTHESIS [J].
OVERMAN, LE .
ACCOUNTS OF CHEMICAL RESEARCH, 1980, 13 (07) :218-224