Anti-selective aldol reactions with titanium enolates of N-glycolyloxazolidinethiones

被引：82

作者：

Crimmins, MT ^{[1
]}

McDougall, PJ ^{[1
]}

机构：

[1] Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 04期

关键词：

D O I：

10.1021/ol034001i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A highly diastereoselective anti aldol addition utilizing a variety of N-glycolyloxazolidinethiones has been developed. Enolization of an N-glycolyloxazolidinethione with titanium (IV) chloride and (-)-sparteine followed by addition of an aldehyde activated with additional TiCl4 resulted in highly anti-selective aldol additions, typically with no observable syn isomers. Allyl-protected glycolates demonstrated the highest levels of selection and yields, although O-benzyl and O-methyl glycolyloxazolidinethiones also performed well.

引用

页码：591 / 594

页数：4

共 15 条

[1] Highly selective syn glycolate aldol reactions with boron enolates of Masamune norephedrine esters [J].

Andrus, MB ;

Sekhar, BBVS ;

Turner, TM ;

Meredith, EL .

TETRAHEDRON LETTERS, 2001, 42 (41) :7197-7201

[2] Anti-selective glycolate aldol additions with an oxapyrone boron enolate [J].

Andrus, MB ;

Sekhar, BBVS ;

Meredith, EL ;

Dalley, NK .

ORGANIC LETTERS, 2000, 2 (19) :3035-3037

[3] SELECTIVE CLEAVAGE OF ALLYL ETHERS UNDER MILD CONDITIONS BY TRANSITION-METAL REAGENTS [J].

COREY, EJ ;

SUGGS, JW .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (18) :3224-3224

[4] An efficient, general asymmetric synthesis of carbocyclic nucleosides: Application of an asymmetric aldol/ring-closing metathesis strategy [J].

Crimmins, MT ;

King, BW ;

Zuercher, WJ ;

Choy, AL .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (25) :8499-8509

[5] Asymmetric aldol additions:: Use of titanium tetrachloride and (-)-sparteine for the soft enolization of N-acyl oxazolidinones, oxazolidinethiones, and thiazolidinethiones [J].

Crimmins, MT ;

King, BW ;

Tabet, EA ;

Chaudhary, K .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (03) :894-902

[6] Asymmetric aldol-ring-closing metathesis strategy for the enantioselective construction of six- to nine-membered oxygen heterocycles [J].

Crimmins, MT ;

Choy, AL .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (22) :7548-7549

[7] Total Synthesis of (+)-prelaureatin and (+)-laurallene [J].

Crimmins, MT ;

Tabet, EA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (23) :5473-5476

[8] ASYMMETRIC-SYNTHESIS OF CALYCULIN-A .2. THE C-26-C-37 GAMMA-AMINO ACID FRAGMENTS [J].

EVANS, DA ;

GAGE, JR ;

LEIGHTON, JL ;

KIM, AS .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) :1961-1963

[9] ENANTIOSELECTIVE ALDOL CONDENSATIONS .2. ERYTHRO-SELECTIVE CHIRAL ALOL CONDENSATIONS VIA BORON ENOLATES [J].

EVANS, DA ;

BARTROLI, J ;

SHIH, TL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) :2127-2129

[10] CHEMISTRY OF TRICARBONYL HEMIKETALS AND APPLICATION OF EVANS TECHNOLOGY TO THE TOTAL SYNTHESIS OF THE IMMUNOSUPPRESSANT (-)-FK-506 [J].

JONES, TK ;

REAMER, RA ;

DESMOND, R ;

MILLS, SG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (08) :2998-3017

← 1 2 →