Synthesis of primary amines via nucleophilic addition of organometallic reagents to aldimines on solid support

被引：33

作者：

Katritzky, AR ^{[1
]}

Xie, LH ^{[1
]}

Zhang, GF ^{[1
]}

Griffith, M ^{[1
]}

Watson, K ^{[1
]}

Kiely, JS ^{[1
]}

机构：

[1] TREGA BIOSCI INC,SAN DIEGO,CA 92121

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 40期

关键词：

D O I：

10.1016/S0040-4039(97)01639-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Resin-immobilized aldimines 5, derived from the condensation of amine-functionalized Rink polystyrene resin with aldehydes, react with Grignard reagents, lithium reagents or LiBH4 to afford a wide variety of primary amines in good to excellent yields upon trifluoroacetic acid cleavage. In this amine synthesis, Rink resin functions both as a solid support and as a NH protecting group. (C) 1997 Elsevier Science Ltd.

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页码：7011 / 7014

页数：4

相关论文

共 21 条

[1] THE ACTIVATION OF IMINES TO NUCLEOPHILIC-ATTACK BY GRIGNARD-REAGENTS [J].

BROOK, MA ;

JAHANGIR .

SYNTHETIC COMMUNICATIONS, 1988, 18 (09) :893-898

[2]

CHENERA B, 1995, J AM CHEM SOC, V117, P11999

[3] SYNTHESIS OF SECONDARY AND TERTIARY CARBINAMINES FROM N-ALKYLIDENEARENESULFENAMIDES AND ALKYLLITHIUM AND ARYLLITHIUM REAGENTS [J].

DAVIS, FA ;

MANCINELLI, PA .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (02) :398-399

[4] THE MECHANISM OF HYDROXYLATION OF ORGANOMETALLIC REAGENTS BY 2-SULFONYLOXAZIRIDINES [J].

DAVIS, FA ;

WEI, J ;

SHEPPARD, AC ;

GUBERNICK, S .

TETRAHEDRON LETTERS, 1987, 28 (43) :5115-5118

[5] APPLICATIONS OF COMBINATORIAL TECHNOLOGIES TO DRUG DISCOVERY .1. BACKGROUND AND PEPTIDE COMBINATORIAL LIBRARIES [J].

GALLOP, MA ;

BARRETT, RW ;

DOWER, WJ ;

FODOR, SPA ;

GORDON, EM .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (09) :1233-1251

[6] APPLICATIONS OF COMBINATORIAL TECHNOLOGIES TO DRUG DISCOVERY .2. COMBINATORIAL ORGANIC-SYNTHESIS, LIBRARY SCREENING STRATEGIES, AND FUTURE-DIRECTIONS [J].

GORDON, EM ;

BARRETT, RW ;

DOWER, WJ ;

FODOR, SPA ;

GALLOP, MA .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (10) :1385-1401

[7] PREPARATION OF PRIMARY AMINES AND 2-AZETIDINONES VIA N-TRIMETHYLSILYL IMINES [J].

HART, DJ ;

KANAI, K ;

THOMAS, DG ;

YANG, TK .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (03) :289-294

[8]

HIRAO A, 1982, SYNTHESIS-STUTTGART, P461

[9]

HOUGHTEN R, 1986, Patent No. 4631211

[10] ORALLY POTENT HUMAN RENIN INHIBITORS DERIVED FROM ANGIOTENSINOGEN TRANSITION-STATE - DESIGN, SYNTHESIS, AND MODE OF INTERACTION [J].

IIZUKA, K ;

KAMIJO, T ;

HARADA, H ;

AKAHANE, K ;

KUBOTA, T ;

UMEYAMA, H ;

ISHIDA, T ;

KISO, Y .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (10) :2707-2714