Allylation and highly diastereoselective syn or anti crotylation of N-toluenesulfonylimines using potassium allyl- and crotyltrifluoroborates

被引：74

作者：

Li, SW ^{[1
]}

Batey, RA ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada

来源：

CHEMICAL COMMUNICATIONS | 2004年 / 12期

关键词：

D O I：

10.1039/b403759f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Air and moisture stable potassium allyl- and crotyltrifluoroborates undergo addition to N-sulfonyl and N-sulfinyl aldimines in the presence of Lewis acids, to provide the corresponding homoallylic amines in high yields and excellent diastereoselectivity.

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页码：1382 / 1383

页数：2

相关论文

共 39 条

[1] Diastereoselective addition of allylmetal compounds to imines derived from (S)-1-phenylethanamine [J].

Alvaro, G ;

Boga, C ;

Savoia, D ;

UmaniRonchi, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (09) :875-882

[2]

Arend M, 1999, ANGEW CHEM INT EDIT, V38, P2873, DOI 10.1002/(SICI)1521-3773(19991004)38:19<2873::AID-ANIE2873>3.0.CO

[3]

2-P

[4] ENANTIOSELECTIVE SYNTHESIS OF HOMOALLYLIC AMINES BY ADDITION OF ALLYLMETAL REAGENTS TO IMINES DERIVED FROM (S)-VALINE ESTERS [J].

BASILE, T ;

BOCOUM, A ;

SAVOIA, D ;

UMANIRONCHI, A .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (25) :7766-7773

[5] Potassium allyl- and crotyltrifluoroborates: Stable and efficient agents for allylation and crotylation [J].

Batey, RA ;

Thadani, AN ;

Smil, DV .

TETRAHEDRON LETTERS, 1999, 40 (23) :4289-4292

[6]

Batey RA, 2000, SYNTHESIS-STUTTGART, P990

[7] Additions of organometallic reagents to C=N bonds: Reactivity and selectivity [J].

Bloch, R .

CHEMICAL REVIEWS, 1998, 98 (04) :1407-1438

[8]

Chen GM, 1999, ANGEW CHEM INT EDIT, V38, P825, DOI 10.1002/(SICI)1521-3773(19990315)38:6<825::AID-ANIE825>3.0.CO

[9]

2-V

[10] Asymmetric synthesis of chiral amines by highly diastereoselective 1,2-additions of organometallic reagents to N-tert-butanesulfinyl imines [J].

Cogan, DA ;

Liu, GC ;

Ellman, J .

TETRAHEDRON, 1999, 55 (29) :8883-8904

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