ZrCl4 as an efficient catalyst for a novel one-pot protection/deprotection synthetic methodology

被引：35

作者：

Singh, Surendra ^{[1
]}

Duffy, Colm D. ^{[1
]}

Shah, Syed Tasadaque A. ^{[1
]}

Guiry, Patrick J. ^{[1
]}

机构：

[1] Univ Coll Dublin, UCD Conway Inst, Sch Chem & Chem Biol, Ctr Synth & Chem Biol, Dublin 4, Ireland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 16期

关键词：

D O I：

10.1021/jo800932t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A catalytic quantity of ZrCl4 (20 mol %) was found to be an efficient catalyst for the one-pot esterification and deprotection of (5S,6R)-5,6-diacetoxyoct-7-enoic acid in good yields (44-62%) with a lactone formed as a minor byproduct. ZrCl4 (10-20 mol %) was also sufficient to deprotect 1,3-dioxalane, bis-TBDMS ethers, and diacetate functional groups in excellent yields of up to 93%. ZrCl4 (1-10 mol %) also promoted diol protection as the acetonide in 90% yield and acted as a trans-esterification catalyst for a range of esters.

引用

收藏

页码：6429 / 6432

页数：4

相关论文

共 61 条

[1] TETRAFLUOROBORIC ACID, AN EFFICIENT CATALYST IN CARBOHYDRATE PROTECTION AND DEPROTECTION REACTIONS [J].

ALBERT, R ;

DAX, K ;

PLESCHKO, R ;

STUTZ, AE .

CARBOHYDRATE RESEARCH, 1985, 137 (MAR) :282-290

[2] Clay catalyzed acetonation: A simple method for the preparation of isopropylidene carbohydrates [J].

Asakura, J ;

Matsubara, Y ;

Yoshihara, M .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1996, 15 (02) :231-239

[3] Highly efficient and chemoselective cleavage of prenyl ethers using ZrCl4/NaBH4 [J].

Babu, KS ;

Raju, BC ;

Srinivas, PV ;

Rao, JM .

TETRAHEDRON LETTERS, 2003, 44 (12) :2525-2528

[4] Selective oxidation of sulfides to sulfoxides and sulfones using hydrogen peroxide (H2O2) in the presence of zirconium tetrachloride [J].

Bahrami, K .

TETRAHEDRON LETTERS, 2006, 47 (12) :2009-2012

[5] Facile and selective deprotection of aryl acetates using sodium perborate under mild and neutral conditions [J].

Bandgar, BP ;

Uppalla, LS ;

Sadavarte, VS ;

Patil, SV .

NEW JOURNAL OF CHEMISTRY, 2002, 26 (10) :1273-1276

[6] A mild procedure for rapid and selective deprotection of aryl acetates using natural kaolinitic clay as a reusable catalyst [J].

Bandgar, BP ;

Uppalla, LS ;

Sagar, AD ;

Sadavarte, VS .

TETRAHEDRON LETTERS, 2001, 42 (06) :1163-1165

[7] Zirconium(IV) chloride as a new, highly efficient, and reusable catalyst for acetylation of phenols, thiols, amines, and alcohols under solvent-free conditions [J].

Chakraborti, AK ;

Gulhane, R .

SYNLETT, 2004, (04) :627-630

[8] ZrCl4 as a new and efficient catalyst for the opening of epoxide rings by amines [J].

Chakraborti, AK ;

Kondaskar, A .

TETRAHEDRON LETTERS, 2003, 44 (45) :8315-8319

[9] A mild and chemoselective method for deprotection of aryl acetates and benzoates under non-hydrolytic condition [J].

Chakraborti, AK ;

Sharma, L ;

Sharma, U .

TETRAHEDRON, 2001, 57 (45) :9343-9346

[10] A novel and efficient deoxygenation of hetero cyclic N-Oxides using ZrCl4/NaBH4 [J].

Chary, KP ;

Mohan, GH ;

Iyengar, DS .

CHEMISTRY LETTERS, 1999, (12) :1339-1340

← 1 2 3 4 5 6 7 →