Synthesis of non-symmetric bis(oxazoline)-containing ligands and their application in the catalytic enantioselective Nozaki-Hiyama-Kishi allylation of benzaldehyde

被引：36

作者：

Hargaden, Griinne C. ^{[1
]}

O'Sullivan, Timothy P. ^{[1
]}

Guiry, Patrick J. ^{[1
]}

机构：

[1] Natl Univ Ireland Univ Coll Dublin, UCD Sch Chem & Chem Biol, UCD Conway Inst, Ctr Synth & Chem Biol, Dublin 4, Ireland

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2008年 / 6卷 / 03期

关键词：

D O I：

10.1039/b715834c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report the good to high-yielding three-step synthesis of non-symmetrical bis(oxazoline)-containing ligands possessing an N-thienylaniline unit. The convergent synthesis employed a palladium-catalysed aryl amination of 2-(2'-bromothiophene)nitrile as the key step, with sixteen ligands prepared in total. These ligands were subsequently applied in the chromium-catalysed enantio selective Nozaki-Hiyama-Kishi allylation of benzaldehyde with an optimal enantioselectivity of 73%.

引用

页码：562 / 566

页数：5

共 52 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] Monodentate phosphines provide highly active catalysts for Pd-catalyzed C-N bond-forming reactions of heteroaromatic halides/amines and (H)N-heterocycles [J].

Anderson, Kevin W. ;

Tundel, Rachel E. ;

Ikawa, Takashi ;

Altman, Ryan A. ;

Buchwald, Stephen L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (39) :6523-6527

[3] TOTAL SYNTHESIS OF PALYTOXIN CARBOXYLIC-ACID AND PALYTOXIN AMIDE [J].

ARMSTRONG, RW ;

BEAU, JM ;

CHEON, SH ;

CHRIST, WJ ;

FUJIOKA, H ;

HAM, WH ;

HAWKINS, LD ;

JIN, H ;

KANG, SH ;

KISHI, Y ;

MARTINELLI, MJ ;

MCWHORTER, WW ;

MIZUNO, M ;

NAKATA, M ;

STUTZ, AE ;

TALAMAS, FX ;

TANIGUCHI, M ;

TINO, JA ;

UEDA, K ;

UENISHI, J ;

WHITE, JB ;

YONAGA, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (19) :7530-7533

[4] Cr(Salen)-catalyzed addition of 1,3-dichloropropene to aromatic aldehydes, a simple access to optically active vinyl epoxides [J].

Bandini, M ;

Cozzi, PG ;

Melchiorre, P ;

Morganti, S ;

Umani-Ronchi, A .

ORGANIC LETTERS, 2001, 3 (08) :1153-1155

[5] Enantioselective catalytic addition of allyl organometallic reagents to aldehydes promoted by [Cr(Salen)]: the hidden role played by weak Lewis acids in metallo-Salen promoted reactions [J].

Bandini, M ;

Cozzi, PG ;

Umani-Ronchi, A .

TETRAHEDRON, 2001, 57 (05) :835-843

[6] Chemo- and enantioselective catalytic addition of propargyl chloride to aldehydes promoted by [Cr(Salen)] complexes [J].

Bandini, M ;

Cozzi, PG ;

Melchiorre, P ;

Tino, R ;

Umani-Ronchi, A .

TETRAHEDRON-ASYMMETRY, 2001, 12 (07) :1063-1069

[7] The first catalytic enantioselective Nozaki-Hiyama-Kishi reaction [J].

Bandini, M ;

Cozzi, PG ;

Umani-Ronchi, A .

POLYHEDRON, 2000, 19 (05) :537-539

[8]

Bandini M., 2000, ANGEW CHEM, V112, P2417

[9] The development of palladium catalysts for C-C and C-heteroatom bond forming reactions of aryl chloride substrates [J].

Bedford, RB ;

Cazin, CSJ ;

Holder, D .

COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2283-2321

[10] 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-+

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