One‐Pot Catalytic Enantioselective Domino Nitro‐Michael/Michael Synthesis of Cyclopentanes with Four Stereocenters

2008/10/01 by Gui‐Ling Zhao, Ismail Ibrahem, Pawel Dziedzic +3
Chemistry · #Asymmetric Hydrogenation and Catalysis #Asymmetric Synthesis and Catalysis #Synthetic Organic Chemistry Methods

paper · doi:10.1002/chem.200801082

openalex publication_date 2008/10/01 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/30

Abstract

A highly enantioselective organocatalytic one-pot synthesis of nitro-, formyl-, and ester-functionalized cyclopentanes with four stereocenters is presented. The cyclopentanes were formed as a predominant diasteroisomer and isolated in high yields with 97-99 % ee.

Related

• Catalytic Enantioselective Ring-Opening Reactions of Cyclopropanes
• Organocatalytic asymmetric desymmetrization of cyclopentene-1,3-diones via a formal diaza–ene reaction with donor–acceptor hydrazones
• Enantioselective synthesis of 1,2-disubstituted thiocyclobutanes via Michael addition
• Tunable thiofumarate stereoselective cycloadditions via aminomefloquine catalysis
• A Type 1 Aldolase, NahE, Catalyzes a Stereoselective Nitro‐Michael Reaction: Synthesis of β‐Aryl‐γ‐nitrobutyric Acids