Stereospecific cross-coupling of α-(thiocarbamoyl)organostannanes with alkenyl, aryl, and heteroaryl iodides

被引:47
作者
Falck, J. R. [1 ]
Patel, Paresh K.
Bandyopadhyay, Anish
机构
[1] Univ Texas, SW Med Ctr, Dept Biochem, Dallas, TX 75390 USA
[2] Univ Texas, SW Med Ctr, Dept Pharmacol, Dallas, TX 75390 USA
关键词
D O I
10.1021/ja064948q
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Racemic and scalemic PTC-protected alpha-hydroxystannanes cross-couple with alkenyl/aryl/heteroaryl iodides in moderate to good yields using copper(I) thiophene-2-carboxylate (CuTC) in THF at or below room temperature. Simple aryl iodides and 1-iodocyclohexene, two classes of electrophiles that typically react sluggishly, are also good substrates. Cross-couplings proceed with retention of configuration at the alkenyl- and stannyl-substituted stereocenters.
引用
收藏
页码:790 / 793
页数:4
相关论文
共 31 条
[1]   Copper-mediated cross-coupling of organostannanes with organic iodides at or below room temperature [J].
Allred, GD ;
Liebeskind, LS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (11) :2748-2749
[2]   INSITU CUPRATE FORMATION VIA TRANSMETALATION BETWEEN VINYLSTANNANES AND HIGHER-ORDER CYANOCUPRATES [J].
BEHLING, JR ;
BABIAK, KA ;
NG, JS ;
CAMPBELL, AL ;
MORETTI, R ;
KOERNER, M ;
LIPSHUTZ, BH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (08) :2641-2643
[3]   C-GLYCOSIDES - PD/CU CO-CATALYZED THIOCARBOXYLATION OF STANNYL GLUCOPYRANOSIDES [J].
BELOSLUDTSEV, YY ;
BHATT, RK ;
FLACK, JR .
TETRAHEDRON LETTERS, 1995, 36 (33) :5881-5882
[4]   Asymmetric Morita-Baylis-Hillman reaction catalyzed by isophoronediamine-derived bis(thio)urea organocatalysts [J].
Berkessel, Albrecht ;
Roland, Katrin ;
Neudoerfl, Jorg M. .
ORGANIC LETTERS, 2006, 8 (19) :4195-4198
[5]   PALLADIUM CATALYZED CROSS-COUPLING AND TANDEM CYCLIZATION-COUPLING OF ALPHA-HALO(THIO)ETHERS WITH ORGANOTINS [J].
BHATT, RK ;
SHIN, DS ;
FALCK, JR ;
MIOSKOWSKI, C .
TETRAHEDRON LETTERS, 1992, 33 (34) :4885-4888
[6]   Reactivity and enantioselectivity in the reactions of scalemic stereogenic α-(N-carbamoyl)alkylcuprates [J].
Dieter, RK ;
Oba, G ;
Chandupatla, KR ;
Topping, CM ;
Lu, K ;
Watson, RT .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (09) :3076-3086
[7]   Enantioselective scandium-catalyzed vinylsilane additions:: A new approach to the synthesis of enantiopure β,γ-unsaturated α-hydroxy acid derivatives [J].
Evans, David A. ;
Aye, Yimon .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (34) :11034-11035
[8]  
Falck JR, 1997, SYNLETT, P481
[9]   Asymmetric synthesis of the stereoisomers of 11,12,15(S)-trihydroxyeicosa-5(Z),8(Z),13(E)-trienoic acid, a potent endothelium-derived vasodilator [J].
Falck, JR ;
Barma, DK ;
Mohapatra, S ;
Bandyopadhyay, A ;
Reddy, KM ;
Qi, JJ ;
Campbell, WB .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (19) :4987-4990
[10]   TIN-COPPER TRANSMETALATION - CROSS-COUPLING OF ALPHA-HETEROATOM-SUBSTITUTED ALKYLTRIBUTYLSTANNANES WITH ORGANOHALIDES [J].
FALCK, JR ;
BHATT, RK ;
YE, JH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (22) :5973-5982