Further improvement on sulfonamide-based ligand for catalytic asymmetric 2-haloallylation and allylation

被引：41

作者：

Zhang, Zhiyu ^{[1
]}

Huang, Jian ^{[1
]}

Ma, Bin ^{[1
]}

Kishi, Yoshito ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 14期

关键词：

D O I：

10.1021/ol801093p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The sulfonamide-based ligand B was found to exhibit an outstanding crystallinity and perform well as a ligand for Cr-mediated catalytic asymmetric 2-haloallylation and allylation. The new ligand has an appealing advantage over the first generation ligand; its high crystallinity allows effective recovery of the ligand from a reaction in a pure form.

引用

页码：3073 / 3076

页数：4

共 45 条

[1] TOTAL SYNTHESIS OF HALICHONDRIN-B AND NORHALICHONDRIN-B [J].

AICHER, TD ;

BUSZEK, KR ;

FANG, FG ;

FORSYTH, CJ ;

JUNG, SH ;

KISHI, Y ;

MATELICH, MC ;

SCOLA, PM ;

SPERO, DM ;

YOON, SK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (08) :3162-3164

[2]

Bandini M, 1999, ANGEW CHEM INT EDIT, V38, P3357, DOI 10.1002/(SICI)1521-3773(19991115)38:22<3357::AID-ANIE3357>3.3.CO

[3]

2-N

[4] [Cr(Salen)] as a 'bridge' between asymmetric catalysis, Lewis acids and redox processes [J].

Bandini, M ;

Cozzi, PG ;

Umani-Ronchi, A .

CHEMICAL COMMUNICATIONS, 2002, (09) :919-927

[5] A highly enantioselective catalyst for the asymmetric Nozaki-Hiyama-Kishi reaction of allylic and vinylic halides [J].

Berkessel, A ;

Menche, D ;

Sklorz, CA ;

Schröder, M ;

Paterson, I .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (09) :1032-+

[6] DOUBLE DIOXANONE-TO-DIHYDROPYRAN REORGANIZATION - CONSTRUCTION OF A C(1)-C(13) ERYTHRONOLIDE TEMPLATE [J].

BURKE, SD ;

LEE, KC ;

SANTAFIANOS, D .

TETRAHEDRON LETTERS, 1991, 32 (32) :3957-3960

[7] ENANTIOSELECTIVE SYNTHESIS OF HOMOALLYLIC ALCOHOLS [J].

CAZES, B ;

VERNIERE, C ;

GORE, J .

SYNTHETIC COMMUNICATIONS, 1983, 13 (01) :73-79

[8] NI(II)/CR(II)-MEDIATED COUPLING REACTION - AN ASYMMETRIC PROCESS [J].

CHEN, CP ;

TAGAMI, K ;

KISHI, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (17) :5386-5387

[9] Synthetic studies on the marine natural product halichondrins [J].

Choi, HW ;

Demeke, D ;

Kang, FA ;

Kishi, Y ;

Nakajima, K ;

Nowak, P ;

Wan, ZK ;

Xie, CY .

PURE AND APPLIED CHEMISTRY, 2003, 75 (01) :1-17

[10] TOTAL SYNTHESIS OF HALICHONDRIN-B FROM COMMON SUGARS - AN F-RING INTERMEDIATE FROM D-GLUCOSE AND EFFICIENT CONSTRUCTION OF THE C1 TO C21 SEGMENT [J].

COOPER, AJ ;

PAN, WX ;

SALOMON, RG .

TETRAHEDRON LETTERS, 1993, 34 (51) :8193-8196

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