Organocatalytic Asymmetric Tandem α‐Aminooxylation–Henry Reactions for the Synthesis of 1, 2‐Diols: Total Synthesis of (–)‐l‐threo‐Sphinganine. Issue 45 (30th November 2017)

• Record Type: Journal Article
• Authors: Garg, Yuvraj; Kaur, Ramandeep; Kumar Pandey, Satyendra
• Is Part Of: European journal of organic chemistry. Issue 45(2017)
• Page Start: 6700
• Page End: 6707
• Publication Date: 2017-11-30
• Subjects: Tandem reactions -- Organocatalysis -- Asymmetric synthesis -- Henry reaction -- Copper -- Total synthesis; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201701289
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A new and rapid asymmetric synthesis of anti ‐ and syn ‐β, γ‐dihydroxynitroalkanes through an organocatalytic tandem α‐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. Abstract : The asymmetric synthesis of anti ‐ and syn ‐β, γ‐dihydroxynitroalkanes from aldehydes through an organocatalytic tandem α‐aminooxylation–Henry reaction is reported. The reaction was also applied to the total synthesis of the antineoplastic and antipsoriatic drug (–)‐l ‐ threo ‐sphinganine.