EXPANDING THE VERSATILITY OF SCHWARTZ REAGENT - HYDROZIRCONATION OF VINYLIC AND ACETYLENIC ACYL SILANES

被引:14
作者
LIPSHUTZ, BH
LINDSLEY, C
BHANDARI, A
机构
[1] Department of Chemistry University of California, Santa Barbara
关键词
D O I
10.1016/S0040-4039(00)76937-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
By virtue of a triisopropylsilyl acyl silane contained within a substrate undergoing hydrozirconation, chemospecificity can be realized favoring addition across the alkene or alkyne, rather than competitive 1,2-addition of hydride to the carbonyl portion of the molecule.
引用
收藏
页码:4669 / 4672
页数:4
相关论文
共 12 条
[1]   A MODIFIED PROCEDURE FOR THE PREPARATION OF CP2ZR(H)CL (SCHWARTZ REAGENT) [J].
BUCHWALD, SL ;
LAMAIRE, SJ ;
NIELSEN, RB ;
WATSON, BT ;
KING, SM .
TETRAHEDRON LETTERS, 1987, 28 (34) :3895-3898
[2]  
Cirillo P. F., 1992, ORG PREP P INT, V24, P553
[3]   SYNTHESIS OF ALPHA-SILYL KETONES VIA 1,3-DITHIANES [J].
COREY, EJ ;
SEEBACH, D ;
FREEDMAN, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (02) :434-&
[4]  
ERKER G, 1989, CHEM SCRIPTA, V29, P451
[5]   SYNTHESIS OF (ALPHA-HYDROXYALKYL)TRIALKYLSILANES VIA A REVERSE BROOK REARRANGEMENT [J].
LINDERMAN, RJ ;
GHANNAM, A .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (12) :2878-2880
[6]   PREPARATION AND USE OF VINYLIC LITHIO CYANOCUPRATES CONTAINING AN OMEGA-ELECTROPHILIC CENTER [J].
LIPSHUTZ, BH ;
KEIL, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (20) :7919-7920
[7]  
NEGISHI E, 1988, SYNTHESIS-STUTTGART, P1
[8]   SYNTHESIS AND CHEMISTRY OF ACYL SILANES [J].
PAGE, PCB ;
KLAIR, SS ;
ROSENTHAL, S .
CHEMICAL SOCIETY REVIEWS, 1990, 19 (02) :147-195
[9]  
RICCI A, 1989, SYNTHESIS-STUTTGART, P647
[10]   FLUORIDE-CATALYZED CONVERSION OF ACYLSILANES TO ALDEHYDES AND KETONES [J].
SCHINZER, D ;
HEATHCOCK, CH .
TETRAHEDRON LETTERS, 1981, 22 (20) :1881-1884