Efficient and selective reduction protocols of the 2,2-dimethyl-1,3-benzodioxan-4-one functional group to readily provide both substituted salicylaldehydes and 2-hydroxybenzyl alcohols

被引：30

作者：

Bajwa, N ^{[1
]}

Jennings, MP ^{[1
]}

机构：

[1] Univ Alabama, Dept Chem, Tuscaloosa, AL 35487 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 09期

关键词：

D O I：

10.1021/jo0601664

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two complementary procedures have been developed that selectively allow for the synthesis of either substituted salicylaldehydes or the corresponding 2-hydroxylbenzyl alcohols upon treatment of the 2,2-dimethyl- 1,3-benzodioxan-4-one functional group with DIBAL-H or LAH, respectively.

引用

收藏

页码：3646 / 3649

页数：4

相关论文

共 27 条

[1]

ALI MA, 1992, CHEM PHARM BULL, V40, P1130, DOI 10.1248/cpb.40.1130

[2] N-substituted (2,3-dihydro-1,4-benzodioxin-2-yl)methylamine derivatives as D2 antagonists/5-HT1A partial agonists with potential as atypical antipsychotic agents [J].

Birch, AM ;

Bradley, PA ;

Gill, JC ;

Kerrigan, F ;

Needham, PL .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (17) :3342-3355

[3] Efficient asymmetric synthesis of (+)-SCH 351448 [J].

Bolshakov, S ;

Leighton, JL .

ORGANIC LETTERS, 2005, 7 (17) :3809-3812

[4]

CASIRAGHI G, 1980, SYNTHESIS-STUTTGART, P124

[5] REDUCTIVE CLEAVAGE OF TERT-BUTYLDIMETHYLSILYL ETHERS BY DIISOBUTYLALUMINUM HYDRIDE [J].

COREY, EJ ;

JONES, GB .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (03) :1028-1029

[6] 3,5-di-(tert-butyl)-6-fluoro-cycloSal-d4TMP -: A pronucleotide with a considerably improved masking group [J].

Ducho, C ;

Wendicke, S ;

Görbig, U ;

Balzarini, J ;

Meier, C .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (24) :4786-4791

[7] TOTAL SYNTHESES OF KS-501, KS-502, AND THEIR ENANTIOMERS [J].

DUSHIN, RG ;

DANISHEFSKY, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (02) :655-659

[8] Synthesis of dendritic metalloporphyrins with distal H-bond donors as model systems for hemoglobin [J].

Felber, B ;

Diederich, F .

HELVETICA CHIMICA ACTA, 2005, 88 (01) :120-153

[9] A SIMPLE APPROACH TOWARDS THE SYNTHESIS OF OXADEAZAFLAVINES [J].

FIGUEROAVILLAR, JD ;

CRUZ, ER .

TETRAHEDRON, 1993, 49 (14) :2855-2862

[10] Asymmetric synthesis of the fully functional macrolide core of salicylihalamide:: Remote control of olefin geometry during RCM [J].

Fürstner, A ;

Thiel, OR ;

Blanda, G .

ORGANIC LETTERS, 2000, 2 (23) :3731-3734