Practical preparation of N-(1-alkynyl)sulfonamides and their remote diastereoselective addition to aldehydes via titanation

被引:72
作者
Hirano, S
Tanaka, R
Urabe, H
Sato, F
机构
[1] Tokyo Inst Technol, Grad Sch Biosci & Biotechnol, Dept Biomol Engn, Midori Ku, Yokohama, Kanagawa 2268501, Japan
[2] Tokyo Inst Technol, Grad Sch Biosci & Biotechnol, Dept Biol Informat, Midori Ku, Yokohama, Kanagawa 2268501, Japan
关键词
D O I
10.1021/ol036396b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aliphatic and aromatic suffonamides were alkynylated with 1-bromo-1-alkynes in the catalytic presence of Cul to give N-(1-alkynyl)sulfonamides in good to excellent yields. The acetylene-titanium complexes generated from N-(1-alkynyl)benzosultams underwent diastereoselective addition to aldehydes.
引用
收藏
页码:727 / 729
页数:3
相关论文
共 30 条
[1]   GROUP-4 METAL-COMPLEXES OF BENZYNES, CYCLOALKYNES, ACYCLIC ALKYNES, AND ALKENES [J].
BUCHWALD, SL ;
NIELSEN, RB .
CHEMICAL REVIEWS, 1988, 88 (07) :1047-1058
[2]   Copper-mediated N-alkynylation of carbamates, ureas, and sulfonamides. A general method for the synthesis of ynamides [J].
Dunetz, JR ;
Danheiser, RL .
ORGANIC LETTERS, 2003, 5 (21) :4011-4014
[3]   Organic chemistry of subvalent transition metal complexes, part 21 - Early transition metal carbenoid reagents in epimetallation and metallative dimerization of unsaturated organic substrates [J].
Eisch, JJ .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 617 (01) :148-157
[4]   A copper-catalyzed C-N bond formation involving sp-hybridized carbons. A direct entry to chiral ynamides via N-alkynylation of amides [J].
Frederick, MO ;
Mulder, JA ;
Tracey, MR ;
Hsung, RP ;
Huang, J ;
Kurtz, KCM ;
Shen, LC ;
Douglas, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (09) :2368-2369
[5]  
Hartwig JF, 1998, ANGEW CHEM INT EDIT, V37, P2046, DOI 10.1002/(SICI)1521-3773(19980817)37:15<2046::AID-ANIE2046>3.0.CO
[6]  
2-L
[7]   Carbon-heteroatom bond-forming reductive eliminations of amines, ethers, and sulfides [J].
Hartwig, JF .
ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (12) :852-860
[8]   SUBSTRATE-DIRECTABLE CHEMICAL-REACTIONS [J].
HOVEYDA, AH ;
EVANS, DA ;
FU, GC .
CHEMICAL REVIEWS, 1993, 93 (04) :1307-1370
[9]  
KIM BH, 1993, TETRAHEDRON, V49, P293
[10]   A general and efficient copper catalyst for the amidation of aryl halides [J].
Klapars, A ;
Huang, XH ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (25) :7421-7428