A scalable synthesis of (R)-3,5-dihydro-4H-dinaphth[2,1-c:12-e]azepine

被引：20

作者：

Ikunaka, M

Maruoka, K

Okuda, Y

Ooi, T

机构：

[1] Nagase & Co Ltd, Res & Dev Ctr, Second Labs, Nishi Ku, Kobe, Hyogo 6512241, Japan

[2] Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan

[3] Nagase ChemteX Corp, BioFine Chem Div, Prod Dev Sect 4, Nishi Ku, Kobe, Hyogo 6512241, Japan

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2003年 / 7卷 / 05期

关键词：

D O I：

10.1021/op034067t

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Environmentally benign scalable procedures are developed to supply enantiomerically pure (R)-3,5-dihydro-4H-dinaphth[2,1-c:1'2'-e]azepine 1 as its hydrogen oxalate salt in a five-step overall yield of 41%, which consist of the following: (1) his O-triflation of (R)-1,1'-bi-2-naphthol 8 [(CF3SO2)(2)O, pyridine, PhMe; quantitative yield]; (2) Kumada's cross-coupling [MeMgI, NiCl2(dppp), tent-BuOMe; 96% yield]; (3) radical bromination [N-bromosuccinimide, 2,2'-azobisisobutyronitrile, cyclohexane; 54% yield]; (4) cyclization [allylamine, Et3N, THF, 86%]; (5) N-deallylation [1,3-dimethylbarbituric acid, Pd(OAc)(2), Ph3P, PhMe] followed by crystalline salt formation with oxalic acid (overall 92% yield).

引用

收藏

页码：644 / 648

页数：5

相关论文

共 32 条

[1] Catalytic asymmetric synthesis of epoxides mediated by chiral iminium salts [J].

Aggarwal, VK ;

Wang, MF .

CHEMICAL COMMUNICATIONS, 1996, (02) :191-192

[2] SYNTHESIS OF CHIRAL 2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL (BINAP) VIA A NOVEL NICKEL-CATALYZED PHOSPHINE INSERTION [J].

CAI, DW ;

PAYACK, JF ;

BENDER, DR ;

HUGHES, DL ;

VERHOEVEN, TR ;

REIDER, PJ .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (23) :7180-7181

[3] SIMPLE AND EFFICIENT RESOLUTION OF 1,1'-BI-2-NAPHTHOL [J].

CAI, DW ;

HUGHES, DL ;

VERHOEVEN, TR ;

REIDER, PJ .

TETRAHEDRON LETTERS, 1995, 36 (44) :7991-7994

[4] Practical synthesis of aryl triflates under aqueous conditions [J].

Frantz, DE ;

Weaver, DG ;

Carey, JP ;

Kress, MH ;

Dolling, UH .

ORGANIC LETTERS, 2002, 4 (26) :4717-4718

[5] MILD AND SELECTIVE PALLADIUM(0)-CATALYZED DEALLYLATION OF ALLYLIC AMINES - ALLYLAMINE AND DIALLYLAMINE AS VERY CONVENIENT AMMONIA EQUIVALENTS FOR THE SYNTHESIS OF PRIMARY AMINES [J].

GARROHELION, F ;

MERZOUK, A ;

GUIBE, F .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (22) :6109-6113

[6] Synthesis of carbohelicenes and derivatives by "carbenoid couplings" [J].

Gingras, M ;

Dubois, F .

TETRAHEDRON LETTERS, 1999, 40 (07) :1309-1312

[7] Synthesis of a chiral azodicarboxamide containing abridging binaphthyl moiety: Electrophilic amination reactions of achiral ester enolates [J].

Harris, JM ;

McDonald, R ;

Vederas, JC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (22) :2669-2674

[8] ASYMMETRIC-SYNTHESIS OF ERYTHRO AND THREO ALPHA-SUBSTITUTED BETA-AMINO ESTERS [J].

HAWKINS, JM ;

LEWIS, TA .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (03) :649-652

[9] ASYMMETRIC MICHAEL REACTIONS OF 3,5-DIHYDRO-4H-DINAPHTH[2,1-C-1',2'-E]AZEPINE WITH METHYL CROTONATE [J].

HAWKINS, JM ;

FU, GC .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (14) :2820-2822

[10] AN ASYMMETRIC AMMONIA SYNTHON FOR MICHAEL ADDITIONS [J].

HAWKINS, JM ;

LEWIS, TA .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) :2114-2121

← 1 2 3 4 →