Synthesis of chiral sulfoximines derived from 3-aminoquinazolinones and their catalysis of enantioselective diethylzinc addition to aldehydes

被引：7

作者：

Karabuga, Semistan ^{[2
]}

Cakici, Murat ^{[3
]}

Kazaz, Cavit ^{[3
]}

Sahin, Ertan ^{[3
]}

Kilic, Hamdullah ^{[3
]}

Ulukanli, Sabri ^{[1
]}

机构：

[1] Osmaniye Korkut Ata Univ, Fac Sci & Letters, Dept Chem, TR-80000 Osmaniye, Turkey

[2] Kahramanmaras Sutcu Imam Univ, Fac Sci & Letters, Dept Chem, TR-46100 Kahramanmaras, Turkey

[3] Ataturk Univ, Fac Sci, Dept Chem, TR-25240 Erzurum, Turkey

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2011年 / 9卷 / 22期

关键词：

CONTROLLED DIASTEREOSELECTIVE AZIRIDINATION; TRANSITION-STATE GEOMETRY; ASYMMETRIC-SYNTHESIS; C-1-SYMMETRIC AMINOSULFOXIMINES; BUTHIONINE SULFOXIMINE; STYRENE DERIVATIVES; LIGANDS; ALKENES; BENZOTHIAZINES; 3-ACETOXYAMINOQUINAZOLINONES;

D O I：

10.1039/c1ob06205k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of sulfoxides were sulfoximinated using oxidative addition of 3-aminoquinazolinones by lead tetraacetate in the presence of hexamethyldisilazane. They were applied for the first time in catalytic enantioselective addition to aromatic aldehydes with a product enantiopurity (ee) of 92% in the case of 2-methoxybenzaldehyde.

引用

页码：7887 / 7896

页数：10

共 50 条

[1] 3-Aminoquinazolinones as chiral ligands in catalytic enantioselective diethylzinc and phenylacetylene addition to aldehydes
Karabuga, Semistan
Karakaya, Idris
Ulukanli, Sabri
[J]. TETRAHEDRON-ASYMMETRY, 2014, 25 (10-11) : 851 - 855
[2] Synthesis of Chiral Pyridylphenols for the Enantioselective Addition of Diethylzinc to Aldehydes
Wu, Pei-Shan
Chen, Chinpiao
[J]. JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2012, 59 (06) : 768 - 781
[3] New chiral ligands derived from (+) and (-)-α-pinene for the enantioselective addition of diethylzinc to aldehydes
Frensch, Gustavo
Labes, Ricardo
Wosch, Celso Luiz
Munaretto, Laieli dos Santos
Salome, Kahlil Schwanka
Guerrero, Palimecio G., Jr.
Marques, Francisco A.
[J]. TETRAHEDRON LETTERS, 2016, 57 (03) : 420 - 422
[4] Synthesis of chiral ligands derived from the Betti base and their use in the enantioselective addition of diethylzinc to aromatic aldehydes
Lu, J
Xu, XN
Wang, C
He, HG
Hu, YF
Hu, HW
[J]. TETRAHEDRON LETTERS, 2002, 43 (46) : 8367 - 8369
[5] A Systematic Study of Chiral Homoprolinols and Their Derivatives in the Catalysis of Enantioselective Addition of Diethylzinc to Aldehydes
Liu, Chang-Lu
Wei, Chang-Yong
Wang, Shi-Wen
Peng, Yun-Gui
[J]. CHIRALITY, 2011, 23 (10) : 921 - 928
[6] New chiral ligands derived from (S)-leucine for the enantioselective addition of diethylzinc to aldehydes
Kawanami, Y
Mitsuie, T
Miki, M
Sakamoto, T
Nishitani, K
[J]. TETRAHEDRON, 2000, 56 (02) : 175 - 178
[7] SYNTHESIS OF CHIRAL CATALYSTS FOR THE ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO AROMATIC-ALDEHYDES
STINGL, K
MARTENS, J
[J]. SYNTHETIC COMMUNICATIONS, 1992, 22 (19) : 2745 - 2756
[8] Synthesis and application of oxadiazines as chiral ligands for the enantioselective addition of diethylzinc to aldehydes
Dean, Melissa A.
Hitchcock, Shawn R.
[J]. TETRAHEDRON-ASYMMETRY, 2010, 21 (20) : 2471 - 2478
[9] Synthesis of new chiral β-amino alcohols derived from isomannide and their application to the catalytic enantioselective addition of diethylzinc to aldehydes
Cho, BT
Kang, SK
[J]. BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2005, 26 (07) : 1101 - 1103
[10] Enantioselective diethylzinc addition to aldehydes using azetidine-derived chiral catalysts
Hermsen, PJ
Cremers, JGO
Thijs, L
Zwanenburg, B
[J]. TETRAHEDRON LETTERS, 2001, 42 (25) : 4243 - 4245

← 1 2 3 4 5 →