Kinetic resolution and unusual regioselectivity in palladium-catalyzed allylic alkylations with a chiral P,S ligand

被引：86

作者：

Faller, JW ^{[1
]}

Wilt, JC ^{[1
]}

Parr, J ^{[1
]}

机构：

[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 08期

关键词：

D O I：

10.1021/ol0497382

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Effective kinetic resolutions of acyclic allylic acetates and benzoates have been obtained using a palladium/(S)-BINAP(S) catalyst system. Unusually large preferences for the formation of branched alkylation products from 3-but-2-enyl and crotyl substrates have been observed.

引用

收藏

页码：1301 / 1304

页数：4

相关论文

共 60 条

[1]

Acemoglu L, 2001, ADV SYNTH CATAL, V343, P75, DOI 10.1002/1615-4169(20010129)343:1<75::AID-ADSC75>3.0.CO

[2]

2-W

[3]

AKERMARK B, 1984, ORGANOMETALLICS, V3, P679

[4] A new P,S-Chiral auxiliary derived from thioglucose. X-ray structure of a palladium 1,3-diphenylallyl complex with a strongly rotated allyl ligand [J].

Albinati, A ;

Pregosin, PS ;

Wick, K .

ORGANOMETALLICS, 1996, 15 (10) :2419-2421

[5] Use of tricyclohexylphosphine to control regiochemistry in palladium-catalyzed allylic alkylation [J].

Blacker, AJ ;

Clarke, ML ;

Loft, MS ;

Williams, JMJ .

ORGANIC LETTERS, 1999, 1 (12) :1969-1971

[6] MECHANISTIC AND SYNTHETIC STUDIES IN CATALYTIC ALLYLIC ALKYLATION WITH PALLADIUM COMPLEXES OF 1-(2-DIPHENYLPHOSPHINO-1-NAPHTHYL)ISOQUINOLINE [J].

BROWN, JM ;

HULMES, DI ;

GUIRY, PJ .

TETRAHEDRON, 1994, 50 (15) :4493-4506

[7] Structural and kinetic effects of chloride ions in the palladium-catalyzed allylic substitutions [J].

Cantat, T ;

Génin, E ;

Giroud, C ;

Meyer, G ;

Jutand, A .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 687 (02) :365-376

[8] Towards a synthesis of epothilone A: asymmetric synthesis of C(1)-C(6) and C(7)-(15) fragments [J].

Chandrasekhar, S ;

Reddy, CR .

TETRAHEDRON-ASYMMETRY, 2002, 13 (03) :261-268

[9] Diphosphine mono-sulfides:: readily available chiral monophosphines [J].

Chapman, CJ ;

Frost, CG ;

Gill-Carey, MP ;

Kociok-Köhn, G ;

Mahon, MF ;

Weller, AS ;

Willis, MC .

TETRAHEDRON-ASYMMETRY, 2003, 14 (06) :705-710

[10] Regioselectivity of the nucleophilic addition to (η3-allyl) palladium complexes.: A theoretical study [J].

Delbecq, F ;

Lapouge, C .

ORGANOMETALLICS, 2000, 19 (14) :2716-2723

← 1 2 3 4 5 6 →