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

[21]

Hoffmann RW, 2000, HETEROCYCLES, V52, P121

[22]

HOFFMANN RW, 2001, ACS SYM SER, V783, P160

[23]

HOFFMANN RW, 2001, HETEROCYCLES, V25, P102

[24] REACTION OF SECONDARY ACETAMIDES WITH N-DICHLOROMETHYLENE-N,N-DIMETHYLAMMONIUM CHLORIDE [J].

JANOUSEK, Z ;

VIEHE, HG ;

COLLARD, J .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1972, 11 (10) :917-&

[25] Reactions of 1-acylamino-1-(trimethylsiloxy)alkanes: Versatile precursors to acylimines [J].

Johnson, AP ;

Luke, RWA ;

Boa, AN .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (09) :895-905

[26]

KATRITZKY AR, 1995, SYNTHESIS-STUTTGART, P503

[27] AMINO-ACIDS AS PRECURSORS TO INDOLIZIDINE ALKALOIDS - DPPA-PROMOTED DECARBONYLATION OF A BICYCLIC AMINO-ACID - AN EASY ENTRY TO HYDROXYLATED INDOLIZIDINES [J].

MARTINLOPEZ, MJ ;

BERMEJOGONZALEZ, F .

TETRAHEDRON LETTERS, 1994, 35 (47) :8843-8846

[28] BETA-BORONATE CARBONYL DERIVATIVES - SYNTHESIS AND EVIDENCE FOR THE INTERVENTION OF BORONATE ATE-COMPLEXES IN ENOLATE ALKYLATIONS [J].

MEARS, RJ ;

WHITING, A .

TETRAHEDRON, 1993, 49 (01) :177-186

[29] Synthesis, structure and comparative stability of β-hydrazono, oximino methyl ether and imino boronates [J].

Mears, RJ ;

Sailes, HE ;

Watts, JP ;

Whiting, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (19) :3250-3263

[30] A VERSATILE NEW SYNTHESIS OF QUINOLINES AND RELATED FUSED PYRIDINES .12. A GENERAL-SYNTHESIS OF 2-CHLOROPYRIDINES AND 2-PYRIDONES [J].

METHCOHN, O ;

WESTWOOD, KT .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (06) :1173-1182

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