One-pot synthesis of new chiral sulfides and selenides containing oxazolidines: Catalyst in the enantioselective addition of diethylzinc to benzaldehyde

被引：40

作者：

Braga, AL ^{[1
]}

Rodrigues, OED

Paixao, MW

Appelt, HR

Silveira, CC

Bottega, DP

机构：

[1] Univ Fed Santa Maria, Dept Quim, BR-97105900 Santa Maria, RS, Brazil

[2] Ctr Univ Franciscano, BR-97010032 Santa Maria, RS, Brazil

来源：

SYNTHESIS-STUTTGART | 2002年 / 16期

关键词：

sulfur; selenium; stereoselective synthesis; asymmetric catalysis; zinc;

D O I：

10.1055/s-2002-35225

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new easily accessible class of chiral sulfides 1 and selenides 2 containing oxazolidine was prepared from amino acids. They were used as chiral ligands in the catalytic asymmetric addition of diethylzinc to benzaldehyde to give the corresponding secondary alcohols in up to 80% ee with an R-configuration.

引用

页码：2338 / 2340

页数：3

共 37 条

[1] Concepts for ligand design in asymmetric catalysis: a study of chiral amino thiol ligands
Anderson, JC
Cubbon, R
Harding, M
James, DS
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (19) : 3461 - 3490
[2] ANDRADE LH, 2002, TETRAHEDRON LETT, V43, P2335
[3] New C2-symmetric chiral disulfide ligands derived from (R)-cysteine
Braga, AL
Appelt, HR
Schneider, PH
Rodrigues, OED
Silveira, CC
Wessjohann, LA
[J]. TETRAHEDRON, 2001, 57 (16) : 3291 - 3295
[4] A new functionalized, chiral disulfide derived from L-cysteine:: (R,R)-bis[(3-benzyloxazolan-4-yl)-methane] disulfide as a catalyst in the diethylzinc addition to aldehydes
Braga, AL
Appelt, HR
Schneider, PH
Silveira, CC
Wessjohann, LA
[J]. TETRAHEDRON-ASYMMETRY, 1999, 10 (09) : 1733 - 1738
[5] Enantioselective addition of diethylzinc to benzaldehyde in the presence of sulfur-containing pyridine ligands
Chelucci, G
Berta, D
Fabbri, D
Pinna, GA
Saba, A
Ulgheri, F
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (11) : 1933 - 1940
[6] Enantioselective addition of diethylzinc to aldehydes catalyzed by a new chiral β-amino alcohol derived from D-mannitol
Cho, BT
Chun, YS
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (09) : 1489 - 1492
[7] SYNTHESIS OF CHIRAL BETA-AMINO SULFIDES AND BETA-AMINO THIOLS FROM ALPHA-AMINO-ACIDS
CRAN, GA
GIBSON, CL
HANDA, S
[J]. TETRAHEDRON-ASYMMETRY, 1995, 6 (07) : 1553 - 1556
[8] Scalemic beta-amino sulfide ligands: Use in enantioselective conjugate additions and X-ray analysis of a dimeric copper(I) complex
Cran, GA
Gibson, CL
Handa, S
Kennedy, AR
[J]. TETRAHEDRON-ASYMMETRY, 1996, 7 (09) : 2511 - 2514
[9] Chiral ligands containing heteroatoms .14. 1,3-oxazolidinyl methanols as chiral catalysts in the enantioselective addition of diethylzinc to aldehydes
Falorni, M
Collu, C
Conti, S
Giacomelli, G
[J]. TETRAHEDRON-ASYMMETRY, 1996, 7 (01) : 293 - 299
[10] THIOL AND DISULFIDE DERIVATIVES OF EPHEDRA ALKALOIDS .2. A MECHANISTIC STUDY OF THEIR EFFECT ON THE ADDITION OF DIETHYL ZINC TO BENZALDEHYDE
FITZPATRICK, K
HULST, R
KELLOGG, RM
[J]. TETRAHEDRON-ASYMMETRY, 1995, 6 (08) : 1861 - 1864

← 1 2 3 4 →