Allylation of unactivated ketones by tetraallyltin accelerated by phenol. Application to asymmetric allylation using a tetraallyltin-BINOL system

被引：38

作者：

Yasuda, M ^{[1
]}

Kitahara, N ^{[1
]}

Fujibayashi, T ^{[1
]}

Baba, A ^{[1
]}

机构：

[1] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

来源：

CHEMISTRY LETTERS | 1998年 / 08期

关键词：

D O I：

10.1246/cl.1998.743

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The tetraallyltin-phenol system was mild and effective for allylation of unactivated ketones, giving tertiary alcohols in high yields. The asymmetric allylation was achieved by a tetraallyltin-homochiral BINOL (1,1'-bi-2-naphthol) system. The addition of methanol raised the enantioselectivity to afford the tertiary homoallylic alcohol up to 60% ee.

引用

页码：743 / 744

页数：2

共 36 条

[1]

ABEL EW, 1975, J ORGANOMET CHEM, V84, P199, DOI 10.1016/S0022-328X(00)90032-9

[2]

Angell RM, 1997, CHEM COMMUN, P919

[3] Solvent-mediated allylation of carbonyl compounds with allylic stannanes [J].

Cokley, TM ;

Harvey, PJ ;

Marshall, RL ;

McCluskey, A ;

Young, DJ .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (07) :1961-1964

[4] CATALYTIC ASYMMETRIC-SYNTHESIS OF HOMOALLYLIC ALCOHOLS [J].

COSTA, AL ;

PIAZZA, MG ;

TAGLIAVINI, E ;

TROMBINI, C ;

UMANIRONCHI, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) :7001-7002

[5] ASYMMETRIC ALLYLATION OF ALDEHYDES WITH CHIRAL LEWIS-BASES [J].

DENMARK, SE ;

COE, DM ;

PRATT, NE ;

GRIEDEL, BD .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21) :6161-6163

[6] Catalytic asymmetric synthesis of homoallylic alcohols: Chiral amplification and chiral poisoning in a titanium/BINOL catalyst system [J].

Faller, JW ;

Sams, DWI ;

Liu, X .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (05) :1217-1218

[7]

FURUTA K, 1991, SYNLETT, P561

[8] REVERSIBLE CROTYLSTANNATION OF CARBONYL-COMPOUNDS - CROTYLSTANNATION ABILITY OF BU3-NCLNSNCH2CH=CHCH3(N=0,1,2) COMPOUNDS TOWARDS ACETONE AND BENZALDEHYDE AND C-13 NMR CHARACTERIZATION [J].

GAMBARO, A ;

MARTON, D ;

PERUZZO, V ;

TAGLIAVINI, G .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1981, 204 (02) :191-196

[9] ALLYLBUTYLTIN HALIDES (CH2=CHCH2)SNBU3-NCLN(N=0,1,2,3) - PREPARATION, C-13 NMR CHARACTERIZATION AND ALLYLSTANNYLATION ABILITY TOWARDS KETONES AND ALDEHYDES [J].

GAMBARO, A ;

PERUZZO, V ;

PLAZZOGNA, G ;

TAGLIAVINI, G .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1980, 197 (01) :45-50

[10] Catalytic, enantioselective addition of allylsilanes to aldehydes: Generation of a novel, reactive Ti-IV complex from TiF4 [J].

Gauthier, DR ;

Carreira, EM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (20) :2363-2365

← 1 2 3 4 →