Asymmetric Synthesis of Ethoxydienamines in Superbasic Medium Mediated by Chiral Sulfinyl Group

被引：3

作者：

Blangetti, Marco ^{[1
]}

Croce, Gianluca ^{[2
]}

Deagostino, Annamaria ^{[1
]}

Mussano, Eleonora ^{[1
]}

Prandi, Cristina ^{[1
]}

Venturello, Paolo ^{[1
]}

机构：

[1] Univ Turin, Dipartimento Chim Gen & Chim Organ, I-10125 Turin, Italy

[2] Univ Piemonte Orientale Amedeo Avogadro, Dipartimento Sci & Tecnol Avanzate, I-15121 Alessandria, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 06期

关键词：

SULFINIMINES; SULFOXIDES;

D O I：

10.1021/jo1024943

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The direct addition of metalated alkoxydiene 2, obtained from alpha,beta-unsaturated acetal 1 through a LIC-KOR-promoted conjugated elimination reaction, to enantiopure sulfinimines 3 (both R and S N-sulfinyl imines) afforded N-sulfinyl alkoxydienyl amines 4 with high diastereoselectivity. Functionalized enantiopure alkoxydienyl amines 5 were then easily obtained upon the selective removal of the chiral auxiliary under mild conditions. Moreover, the further hydrolysis of the alkoxydienyl moiety gave access to protected enantiopure beta-keto amines 7.

引用

页码：1814 / 1820

页数：7

共 50 条

[21] Asymmetric Intramolecular Pauson-Khand Reaction Mediated by a Remote Sulfenyl or Sulfinyl Group
Garcia Ruano, Jose Luis
Torrente, Esther
Parra, Alejandro
Aleman, Jose
Martin-Castro, Ana M.
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (15): : 6583 - 6599
[22] SYNTHESIS AND REDUCTION OF CHIRAL SULFINYL CYCLOHEXANONES
CARRENO, MC
RUANO, JLG
RUBIO, A
TETRAHEDRON LETTERS, 1987, 28 (41) : 4861 - 4864
[23] ASYMMETRIC SYNTHESIS AT A PYRAMIDAL NITROGEN CENTER IN A CHIRAL MEDIUM
BOYD, DR
NEILL, DC
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (02) : 51 - 52
[24] Design, Synthesis, and Applications of Chiral N-2-Phenyl-2-propyl Sulfinyl Imines for Group-Assisted Purification (GAP) Asymmetric Synthesis
Pindi, Suresh
Wu, Jianbin
Li, Guigen
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (08): : 4006 - 4012
[25] Synthesis of Unfunctionalized Carbonated Fragments Containing Two Vicinal Chiral Centers: Stereocontrolled Benzylation of Vinylsulfones Mediated by a Remote Sulfinyl Group
Garcia Ruano, Jose Luis
Schoepping, Christine
Alvarado, Cuauhtemoc
Aleman, Jose
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (30) : 8968 - 8971
[26] Redox transformation of β-sulfinyl esters for asymmetric synthesis of sulfone-based axially chiral styrenes
Xiang, Shiyu
Lu, Taotao
Liu, Junjun
Zhao, Qingyang
ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (16) : 3975 - 3981
[27] Asymmetric Synthesis of α-Chloro-β-amino-N-sulfinyl Imidates as Chiral Building Blocks
Colpaert, Filip
Mangelinckx, Sven
De Brabandere, Stijn
De Kimpe, Norbert
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (07): : 2204 - 2213
[28] Organocatalytic asymmetric deoxygenation of sulfones to access chiral sulfinyl compounds
Shengli Huang
Zhen Zeng
Nan Zhang
Wenling Qin
Yu Lan
Hailong Yan
Nature Chemistry, 2023, 15 : 185 - 193
[29] Developments of asymmetric synthesis mediated by chiral sulfur reagents
Blot, V
Brière, JF
Davoust, M
Minière, S
Reboul, V
Metzner, P
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2005, 180 (5-6) : 1171 - 1182
[30] Asymmetric Access to Chiral Sulfinyl Compounds as Bioisosteres of Carbonyl Compounds
Wang, Chenxin
Wu, Xinyu
Huang, Jiapian
Liu, Gang
Wu, Jie
SYNTHESIS-STUTTGART, 2024, 56 (17): : 2648 - 2654

← 1 2 3 4 5 →