An aza-payne rearrangement-epoxide ring opening reaction of 2-aziridinemethanols in a one-pot manner: A regio- and stereoselective synthetic route to diastereomerically pure N-protected 1,2-amino alcohols

被引：29

作者：

Ibuka, T ^{[1
]}

Nakai, K ^{[1
]}

Akaji, M ^{[1
]}

Tamamura, H ^{[1
]}

Fujii, N ^{[1
]}

Yamamoto, Y ^{[1
]}

机构：

[1] TOHOKU UNIV, FAC SCI, DEPT CHEM, SENDAI, MIYAGI 980, JAPAN

来源：

TETRAHEDRON | 1996年 / 52卷 / 36期

关键词：

D O I：

10.1016/0040-4020(96)00682-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A regio- and stereoselective synthetic route to diastereomerically pure 1,2-amino alcohols via a one-pot aza-Payne rearrangement - epoxide ring opening reaction of 2-aziridinemethanols is reported. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：11739 / 11752

页数：14

共 56 条

[21] FLUORIDE-ION CATALYZED REDUCTION OF ALDEHYDES AND KETONES WITH HYDROSILANES - SYNTHETIC AND MECHANISTIC ASPECTS AND AN APPLICATION TO THE THREO-DIRECTED REDUCTION OF ALPHA-SUBSTITUTED ALKANONES [J].

FUJITA, M ;

HIYAMA, T .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (23) :5405-5415

[22] BORANES IN SYNTHESIS .6. A NEW SYNTHESIS OF BETA-AMINO ALCOHOLS FROM EPOXIDES - USE OF LITHIUM AMIDES AND AMINOBORANE CATALYSTS TO SYNTHESIZE BETA-AMINO ALCOHOLS FROM TERMINAL AND INTERNAL EPOXIDES IN HIGH-YIELD [J].

HARRIS, CE ;

FISHER, GB ;

BEARDSLEY, D ;

LEE, L ;

GORALSKI, CT ;

NICHOLSON, LW ;

SINGARAM, B .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (25) :7746-7751

[23] SPECTROSCOPIC AND CHEMICAL EVIDENCE FOR THE REVERSIBLE FORMATION OF VINYLCOPPER INTERMEDIATES IN THE STANNYLCUPRATION OF TERMINAL ALKYNES [J].

HUTZINGER, MW ;

SINGER, RD ;

OEHLSCHLAGER, AC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (25) :9397-9398

[24] UNPRECEDENTED REARRANGEMENT REACTION OF 2-AZIRIDINEMETHANOLS WITH LOWER ORDER LITHIUM METHYLCYANOCUPRATE [J].

IBUKA, T ;

NAKAI, K ;

HABASHITA, H ;

FUJII, N ;

GARRIDO, F ;

MANN, A ;

CHOUNAN, Y ;

YAMAMOTO, Y .

TETRAHEDRON LETTERS, 1993, 34 (46) :7421-7424

[25]

IBUKA T, 1994, ANGEW CHEM INT EDIT, V33, P652, DOI 10.1002/anie.199406521

[26] AZA-PAYNE REARRANGEMENT OF ACTIVATED 2-AZIRIDINEMETHANOLS AND 2,3-EPOXY AMINES UNDER BASIC CONDITIONS [J].

IBUKA, T ;

NAKAI, K ;

HABASHITA, H ;

HOTTA, Y ;

TAMAMURA, H ;

FUJII, N ;

MIMURA, N ;

MIWA, Y ;

TAGA, T ;

CHOUNAN, Y ;

YAMAMOTO, Y ;

OTAKA, A .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (07) :2044-2058

[27]

KARRER P, 1948, HELV CHIM ACTA, V31, P1617, DOI 10.1002/hlca.19480310623

[28]

KARRER P, 1949, HELV CHIM ACTA, V32, P1156, DOI 10.1002/hlca.19490320374

[29] SYNTHESIS OF SACCHARIDES AND RELATED POLYHYDROXYLATED NATURAL-PRODUCTS .1. SIMPLE ALDITOLS [J].

KATSUKI, T ;

LEE, AWM ;

MA, P ;

MARTIN, VS ;

MASAMUNE, S ;

SHARPLESS, KB ;

TUDDENHAM, D ;

WALKER, FJ .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (07) :1373-1378

[30] AN ENANTIODIVERGENT SYNTHESIS OF THREO BETA-AMINO ALCOHOLS - PREPARATION OF KEY INTERMEDIATES FOR BESTATIN AND THE RELATED PEPTIDES [J].

KAWABATA, T ;

KIRYU, Y ;

SUGIURA, Y ;

FUJI, K .

TETRAHEDRON LETTERS, 1993, 34 (32) :5127-5130

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