Stereoselective addition of the titanium enolate of N-acetyl (4S)-isopropyl-1,3-thiazolidine-2-thione to five-membered N-acyl iminium ions

被引：16

作者：

Barragán, E ^{[1
]}

Olivo, HF ^{[1
]}

Romero-Ortega, M ^{[1
]}

Sarduy, S ^{[1
]}

机构：

[1] Univ Iowa, Coll Pharm, Div Med & Nat Prod Chem, Iowa City, IA 52242 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 10期

关键词：

D O I：

10.1021/jo050188a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Addition of the chlorotitanium enolate of N-acetyl 4-isopropyl-1,3-thiazolidine-2-thione to five-membered, N-Substituted N-acyl iminium ions furnished the corresponding Mannich-type addition products with good diastereoselectivity and in good yields. The synthetic utility of the addition product 8 was demonstrated in a chemospecific anti-aldol reaction with cinnamaldehyde. By using this strategy, we constructed three contiguous chiral centers with high stereocontrol employing the same chiral auxiliary. X-Ray crystallographic analysis of addition product 2 and aldol product 14 revealed their absolute stereochemistry.

引用

页码：4214 / 4217

页数：4

共 47 条

[1] Diastereoselective addition of chlorotitanium enolate of N-acyl thiazolidinethione to O-methyl oximes:: A novel, stereoselective synthesis of α,β-disubstituted β-amino carbonyl compounds via chiral auxiliary mediated azetine formation [J].

Ambhaikar, NB ;

Snyder, JP ;

Liotta, DC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (13) :3690-3691

[2] DCC/DMAP-mediated coupling of carboxylic acids with oxazolidinones and thiazolidinethiones [J].

Andrade, CKZ ;

Rocha, RO ;

Vercillo, OE ;

Silva, WA ;

Matos, RAF .

SYNLETT, 2003, (15) :2351-2352

[3]

[Anonymous], 1994, Aldrichimica Acta

[4]

[Anonymous], 1994, Org. React

[5]

Arend M, 1998, ANGEW CHEM INT EDIT, V37, P1044, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO

[6]

2-E

[7] Study of the Lewis acid-promoted imines derived from addition of silylenol ethers to glyceraldehyde [J].

Badorrey, R ;

Cativiela, C ;

Díaz-de-Villegas, MD ;

Gálvez, JA .

TETRAHEDRON LETTERS, 2003, 44 (51) :9189-9192

[8] Addition of carbon nucleophiles to cyclic N-acyliminium ions in SDS/water [J].

Camilo, NS ;

Pilli, RA .

TETRAHEDRON LETTERS, 2004, 45 (13) :2821-2823

[9]

COLE DC, 1994, TETRAHEDRON, V50, P9517

[10] Titanium enolates of thiazolidinethione chiral auxiliaries: Versatile tools for asymmetric aldol additions [J].

Crimmins, MT ;

Chaudhary, K .

ORGANIC LETTERS, 2000, 2 (06) :775-777

← 1 2 3 4 5 →