Stereoselective synthesis of alcohols.: Part LV.: Domino hydroformylation-allylboration-hydroformylation reactions to give trans-perhydropyrano[3,2-b]pyridine derivatives

被引：46

作者：

Hoffmann, RW ^{[1
]}

Brückner, D ^{[1
]}

机构：

[1] Univ Marburg, Fachbereich Chem, D-35032 Marburg, Germany

来源：

NEW JOURNAL OF CHEMISTRY | 2001年 / 25卷 / 03期

关键词：

D O I：

10.1039/b009259m

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

N-Allyl-(E)-gamma -aminoallyl boronates 8 and 18, when subjected to hydroformylation conditions, enter into a domino hydroformylation-allylboration-hydroformylation reaction cascade to generate the bicyclic N,O-heterocycles 12 and 20. On reaction of the methallyl compound 8b a stereogenic center is generated in the initial hydroformylation, which controls the relative configuration of the two new stereogenic centers resulting from the allylboration reaction.

引用

页码：369 / 373

页数：5

共 48 条

[1]

[Anonymous], 2000, ORGANIC REACTIONS

[2]

[Anonymous], ANGEW CHEM

[3] DECOMPOSITION OF ARILAZIDES AND PARA-TOSYLAZIDE BY THF NORMAL-BUTYLLITHIUM - A NEW SOURCE OF DIAZOMETHANE [J].

BABUDRI, F ;

DINUNNO, L ;

FLORIO, S ;

VALZANO, S .

TETRAHEDRON, 1984, 40 (10) :1731-1736

[4] A CONFORMATIONAL STUDY OF BAFILOMYCIN-A1 BY X-RAY CRYSTALLOGRAPHY AND NMR TECHNIQUES [J].

BAKER, GH ;

BROWN, PJ ;

DORGAN, RJJ ;

EVERETT, JR ;

LEY, SV ;

SLAWIN, AMZ ;

WILLIAMS, DJ .

TETRAHEDRON LETTERS, 1987, 28 (45) :5565-5568

[5] 3-(4-IODOMETHYL-2-OXO-1-AZETIDINYL)PROPYNOIC ACID TERT-BUTYL ESTER - A NEW BETA-LACTAM DERIVATIVE, SYNTHESIS OF AN YNAMIDE BY REACTION OF 4-IODOMETHYLAZETIDIN-2-ONE WITH THE TERT-BUTYL ESTER OF PROPIOLIC ACID IN THE PRESENCE OF COPPER(I) [J].

BALSAMO, A ;

MACCHIA, B ;

MACCHIA, F ;

ROSSELLO, A ;

DOMIANO, P .

TETRAHEDRON LETTERS, 1985, 26 (34) :4141-4144

[6] THE USE OF B-[(E)-3-(DIPHENYLAMINO)ALLYL[DIISOPINOCAMPHEYLBORANE AS A REAGENT FOR THE STEREOSELECTIVE SYNTHESIS OF ANTI-BETA-DIPHENYLAMINO ALCOHOLS AND TRANS-1-DIPHENYLAMINO-2-(1-HYDROXYALKYL) CYCLOROPANES [J].

BARRETT, AGM ;

SEEFELD, MA .

TETRAHEDRON, 1993, 49 (36) :7857-7870

[7] Convenient asymmetric syntheses of anti-beta-amino alcohols [J].

Barrett, AGM ;

Seefeld, MA ;

White, AJP ;

Williams, DJ .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (08) :2677-2685

[8] CONVERGENCE, MOLECULAR COMPLEXITY, AND SYNTHETIC ANALYSIS [J].

BERTZ, SH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (21) :5801-5803

[9] UBER N-ALPHA-HALOGENALKYL-CARBONSAUREAMIDE .7. DIE UMSETZUNG SCHIFFSCHER BASEN MIT CARBONSAUREHALOGENIDEN [J].

BOHME, H ;

HARTKE, K .

CHEMISCHE BERICHTE-RECUEIL, 1963, 96 (02) :600-&

[10]

BREEDERVELD H, 1960, RECL TRAV CHIM PAY B, V79, P1197

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