Synthesis of sulfonylated amino alcohols and asymmetric addition of diethylzinc to aldehydes catalyzed by titanium complexes

被引：0

作者：

Hui, XP ^{[1
]}

Qiao, RZ ^{[1
]}

Xu, PF ^{[1
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 26卷 / 02期

关键词：

sulfonylated amino alcohol; (+)-10-camphorsulfonyl chloride; diethylzinc; Ti(O-i-Pr)(4);

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Sulfonylated amino alcohols 3 similar to 5 were prepared and the asymmetric addition of diethylzinc to aldehydes catalyzed by titanium complexes of those ligands was carried out. Good enantioselectivities were obtained with ee values up to 91%.

引用

页码：211 / 214

页数：4

共 23 条

[1] Design of diastereomeric self-inhibiting catalysts for control of turnover frequency and enantioselectivity [J].

Balsells, J ;

Walsh, PJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (13) :3250-3251

[2] CHEMISTRY OF OXAZIRIDINES .3. ASYMMETRIC OXIDATION OF ORGANOSULFUR COMPOUNDS USING CHIRAL 2-SULFONYLOXAZIRIDINES [J].

DAVIS, FA ;

JENKINS, RH ;

AWAD, SB ;

STRINGER, OD ;

WATSON, WH ;

GALLOY, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (20) :5412-5418

[3] Salen-derived catalysts containing secondary basic groups in the addition of diethylzinc to aldehydes [J].

DiMauro, EF ;

Kozlowski, MC .

ORGANIC LETTERS, 2001, 3 (19) :3053-3056

[4] Enantioselective catalysis of hetero Diels-Alder reaction and diethylzinc addition using a single catalyst [J].

Du, HF ;

Ding, KL .

ORGANIC LETTERS, 2003, 5 (07) :1091-1093

[5] CHIRAL TITANIUM COMPLEXES FOR ENANTIOSELECTIVE ADDITION OF NUCLEOPHILES TO CARBONYL GROUPS [J].

DUTHALER, RO ;

HAFNER, A .

CHEMICAL REVIEWS, 1992, 92 (05) :807-832

[6] Synthesis of novel C2-symmetric chiral bis(oxazoline) ligands and their application in the enantioselective addition of diethylzinc to aldehydes [J].

Fu, B ;

Du, DM ;

Wang, JB .

TETRAHEDRON-ASYMMETRY, 2004, 15 (01) :119-126

[7] Enantioselective additions of diethylzinc and diphenylzinc to aldehydes using 2-dialkyl-aminomethyl-2′-hydroxy-1,1′-binaphthyls [J].

Ko, DH ;

Kim, KH ;

Ha, DC .

ORGANIC LETTERS, 2002, 4 (21) :3759-3762

[8] The application of chiral aminonaphthols in the enantioselective addition of diethylzinc to aryl aldehydes [J].

Liu, DX ;

Zhang, LC ;

Wang, Q ;

Da, CS ;

Xin, ZQ ;

Wang, R ;

Choi, MCK ;

Chan, ASC .

ORGANIC LETTERS, 2001, 3 (17) :2733-2735

[9] Increased enantioselectivity in the addition of diethylzinc to benzaldehyde by the use of chiral ligands containing the α-phenylethylamino group in combination with achiral ligands [J].

Muñoz-Muñiz, O ;

Juaristi, E .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (10) :3781-3785

[10] Recyclable fluorous chiral ligands and catalysts: asymmetric addition of diethylzinc to aromatic aldehydes catalyzed by fluorous BINOL-Ti complexes [J].

Nakamura, Y ;

Takeuchi, S ;

Okumura, K ;

Ohgo, Y ;

Curran, DP .

TETRAHEDRON, 2002, 58 (20) :3963-3969

← 1 2 3 →