N-isopropylsulfinylimines as useful intermediates in the synthesis of chiral amines:: Expeditive asymmetric synthesis of the calcimimetic (+)-NPS R-568

被引：22

作者：

Fernandez, Inmaculada ^{[1
]}

Valdivia, Victoria ^{[2
]}

Khiar, Noureddine ^{[2
]}

机构：

[1] Univ Seville, Dept Quim Organ & Farmaceut, Fac Farm, E-41012 Seville, Spain

[2] Univ Seville, CSIC, Inst Invest Quim, Seville 41092, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 02期

关键词：

D O I：

10.1021/jo7018703

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] An efficient and high-yielding approach for the asymmetric synthesis of calcimimetic (+)-NPS R-568 (1) has been developed. The key step of the synthesis is the highly diastereoselective addition of methyl Grignard to the (S-S,E)-N-(3-methoxybenzylidene)-2-propanesulfinamide [5(S)], which afforded a single diastereoisomer in high yield in short reaction time.

引用

页码：745 / 748

页数：4

共 26 条

[1]

[Anonymous], TETRAHEDRON-ASYMMETR

[2] Enantioselective synthesis of primary 1-(aryl)alkylamines by nucleophilic 1,2-addition of organolithium reagents to hydroxyoxime ethers and application to asymmetric synthesis of G-protein-coupled receptor ligands [J].

Atobe, M ;

Yamazaki, N ;

Kibayashi, C .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) :5595-5607

[3] Additions of organometallic reagents to C=N bonds: Reactivity and selectivity [J].

Bloch, R .

CHEMICAL REVIEWS, 1998, 98 (04) :1407-1438

[4] Catalytic asymmetric oxidation of tert-butyl disulfide.: Synthesis of tert-butanesulfinamides, tert-butyl sulfoxides, and tert-butanesulfinimines [J].

Cogan, DA ;

Liu, GC ;

Kim, KJ ;

Backes, BJ ;

Ellman, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (32) :8011-8019

[5]

Davis FA, 1998, CHEM SOC REV, V27, P13

[6] Adventures in sulfur-nitrogen [J].

Davis, Franklin A. .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (24) :8993-9003

[7] Applications of tert-butanesulfinamide in the asymmetric synthesis of amines [J].

Ellman, JA .

PURE AND APPLIED CHEMISTRY, 2003, 75 (01) :39-46

[8] N-tert-Butanesulfinyl imines:: Versatile intermediates for the asymmetric synthesis of amines [J].

Ellman, JA ;

Owens, TD ;

Tang, TP .

ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (11) :984-995

[9] ASYMMETRIC-SYNTHESIS OF ALKANESULFINATES AND ARENESULFINATES OF DIACETONE-D-LUCOSE (DAG) - AN IMPROVED AND GENERAL-ROUTE TO BOTH ENANTIOMERICALLY PURE SULFOXIDES [J].

FERNANDEZ, I ;

KHIAR, N ;

LLERA, JM ;

ALCUDIA, F .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (25) :6789-6796

[10] Recent developments in the synthesis and utilization of chiral sulfoxides [J].

Fernández, I ;

Khiar, N .

CHEMICAL REVIEWS, 2003, 103 (09) :3651-3705

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