Organocatalytic Asymmetric Tandem -Aminooxylation-Henry Reactions for the Synthesis of 1,2-Diols: Total Synthesis of (-)-l-threo-Sphinganine

被引：13

作者：

Garg, Yuvraj ^{[1
]}

Kaur, Ramandeep ^{[1
]}

Pandey, Satyendra Kumar ^{[1
,2
]}

机构：

[1] Thapar Univ, Sch Chem & Biochem, Patiala 147001, Punjab, India

[2] Banaras Hindu Univ, Inst Sci, Dept Chem, Varanasi 221005, Uttar Pradesh, India

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 2017卷 / 45期

关键词：

Tandem reactions; Organocatalysis; Asymmetric synthesis; Henry reaction; Copper; Total synthesis; ENANTIOSELECTIVE TOTAL-SYNTHESIS; D-RIBO-PHYTOSPHINGOSINE; ALPHA; BETA-UNSATURATED ALDEHYDES; NITROALDOL REACTIONS; CASCADE REACTION; COMPLEXES; SAFINGOL; LIGAND; DIHYDROXYLATION; SPHINGANINE;

D O I：

10.1002/ejoc.201701289

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new and rapid asymmetric synthesis of anti- and syn-,-dihydroxynitroalkanes through an organocatalytic tandem -aminooxylation-Henry reaction is described. The target diol derivatives were synthesized in good yields, with excellent enantioselectivities, and low to moderate diasteroselectivities, under mild conditions. The synthesis of the antineoplastic and antipsoriatic drug (-)-l-threo-sphinganine demonstrates the synthetic utility of the building blocks generated in the developed reaction.

引用

页码：6700 / 6707

页数：8

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