Enantioselective intermolecular 1,3-dipolar cycloaddition via ester-derived carbonyl ylide formation catalyzed by chiral dirhodium(II) carboxylates

被引：77

作者：

Kitagaki, S ^{[1
]}

Yasugahira, M ^{[1
]}

Anada, M ^{[1
]}

Nakajima, M ^{[1
]}

Hashimoto, S ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Kita Ku, Sapporo, Hokkaido 0600812, Japan

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 31期

关键词：

D O I：

10.1016/S0040-4039(00)00977-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantioselective 1,3-dipolar cycloaddition of the ester-carbonyl ylides derived from methyl 2-(diazoacetyl)benzoate and 3-(diazoacetyl)-2-naphthoate with dipolarophiles has been effected with the aid of dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate], affording cycloadducts in up to 93% ee. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：5931 / 5935

页数：5

共 15 条

[1]

Anada M, 1999, SYNLETT, P1775

[2]

Davies H. M. L., 1997, ALDRICHIM ACTA, V30, P107

[3] Recent advances in asymmetric catalytic metal carbene transformations [J].

Doyle, MP ;

Forbes, DC .

CHEMICAL REVIEWS, 1998, 98 (02) :911-935

[4]

Doyle MP, 1996, ALDRICHIM ACTA, V29, P3

[5] Stereocontrol in intermolecular dirhodium(II)-catalyzed carbonyl ylide formation and reactions. Dioxolanes and dihydrofurans [J].

Doyle, MP ;

Forbes, DC ;

Protopopova, MN ;

Stanley, SA ;

Vasbinder, MM ;

Xavier, KR .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) :7210-7215

[6] Efficient RhII binaphthol phosphate catalysts for enantioselective intramolecular tandem carbonyl ylide formation-cycloaddition of α-diazo-β-keto esters [J].

Hodgson, DM ;

Stupple, PA ;

Johnstone, C .

CHEMICAL COMMUNICATIONS, 1999, (21) :2185-2186

[7] THE REACTION OF DIAZO KETONES IN THE PRESENCE OF METAL-CHELATES .8. THE STEREOCHEMISTRY OF THE 1,3-DIPOLAR CYCLOADDITION OF 1-METHOXY-2-BENZOPYRYLIUM-4-OLATES TO ETHYLENIC DIPOLAROPHILES [J].

IBATA, T ;

JITSUHIRO, K ;

TSUBOKURA, Y .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1981, 54 (01) :240-244

[8] REACTION OF DIAZO KETONES IN THE PRESENCE OF METAL-CHELATES .7. 1,3-DIPOLAR CYCLOADDITION OF 1-METHOXYBENZO[C]PYRYLIUM-4-OLATE WITH ACETYLENIC DIPOLAROPHILES [J].

IBATA, T ;

JITSUHIRO, K .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1979, 52 (12) :3582-3585

[9]

IBATA T, 1976, SCI REP COLLG EN ED, V25, P19

[10] Enantiocontrol in tandem carbonyl ylide formation and intermolecular 1,3-dipolar cycloaddition of α-diazo ketones mediated by chiral dirhodium(II) carboxylate catalyst [J].

Kitagaki, S ;

Anada, M ;

Kataoka, O ;

Matsuno, K ;

Umeda, C ;

Watanabe, N ;

Hashimoto, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (06) :1417-1418

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