CHIRAL SYNTHESIS VIA ORGANOBORANES .36. EXCEPTIONALLY ENANTIOSELECTIVE ALLYLBORATIONS OF REPRESENTATIVE HETEROCYCLIC ALDEHYDES AT -100-DEGREES-C UNDER SALT-FREE CONDITIONS

被引：71

作者：

RACHERLA, US ^{[1
]}

LIAO, Y ^{[1
]}

BROWN, HC ^{[1
]}

机构：

[1] PURDUE UNIV,DEPT CHEM,HC BROWN & RB WETHERHILL LABS CHEM,W LAFAYETTE,IN 47907

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 24期

关键词：

D O I：

10.1021/jo00050a045

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral terpenyl-based allylborane reagents (Ter2*BCH2CH=CH2, 1-3) undergo facile condensation with representative heterocyclic aldehydes (HetCHO) at -100-degrees-C (in the absence of Mg2+ salts) and afford the corresponding homoallylic alcohols (HetCH*(OH)CH2CH=CH2,12-19) in enantiomeric purities approaching 100% ee. A new workup procedure involving 8-hydroxyquinoline (8-HQ) has been utilized for the convenient isolation of the product alcohols.

引用

页码：6614 / 6617

页数：4

共 37 条

[1]

ACHMATOWICZ O, 1981, ORGANIC SYNTHESIS TO, P307

[2] APPLICATIONS OF CROTYLDIISOPINOCAMPHEYLBORANES IN SYNTHESIS - THE TOTAL SYNTHESIS OF NIKKOMYCIN-B [J].

BARRETT, AGM ;

LEBOLD, SA .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (16) :4875-4884

[3] CHIRAL SYNTHESIS VIA ORGANOBORANES .24. B-ALLYLBIS(2-ISOCARANYL)BORANE AS A SUPERIOR REAGENT FOR THE ASYMMETRIC ALLYLBORATION OF ALDEHYDES [J].

BROWN, HC ;

RANDAD, RS ;

BHAT, KS ;

ZAIDLEWICZ, M ;

RACHERLA, US .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (06) :2389-2392

[4]

BROWN HC, 1975, ORGANIC SYNTHESES VI

[5] DIASTEREOSELECTIVE CHLOROCYCLOFUNCTIONALIZATION OF N-ALLYLIC TRICHLOROACETAMIDES - SYNTHESIS OF AN ANALOG AND POTENTIAL PRECURSOR OF RP49532 [J].

COMMERCON, A ;

PONSINET, G .

TETRAHEDRON LETTERS, 1990, 31 (27) :3871-3874

[6]

COPPOLA GM, 1987, ASYMMETRIC SYNTHESIS, P25

[7] ACETOGENINS OF ANNONACEAE .12. MOLVIZARIN AND MOTRILIN - 2 NOVEL CYTOTOXIC BIS-TETRAHYDROFURANIC GAMMA-LACTONE ACETOGENINS FROM ANNONA-CHERIMOLIA [J].

CORTES, D ;

MYINT, SH ;

HOCQUEMILLER, R .

TETRAHEDRON, 1991, 47 (38) :8195-8202

[8] ASYMMETRIC-SYNTHESIS AND ABSOLUTE STEREOCHEMISTRY OF LY248686 [J].

DEETER, J ;

FRAZIER, J ;

STATEN, G ;

STASZAK, M ;

WEIGEL, L .

TETRAHEDRON LETTERS, 1990, 31 (49) :7101-7104

[9]

FANG XP, 1991, HETEROCYCLES, V32, P11

[10] SYNTHESIS OF 1S,2R,3S,4R,5R-METHYL[2,3,4-TRIHYDROXY-5-(HYDROXYMETHYL)CYCLOPENTYL]AMINE - A POTENT ALPHA-MANNOSIDASE INHIBITOR [J].

FARR, RA ;

PEET, NP ;

KANG, MS .

TETRAHEDRON LETTERS, 1990, 31 (49) :7109-7112

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