75658-85-4

Basic information

• Product Name: 3-Oxabicyclo[3.2.0]heptan-2-one, (1S)-
• CAS NO: 75658-85-4
• Molecular Formula: C6H8O2
• Molecular Weight: 112.128
• Mol File: 75658-85-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 3-Oxabicyclo[3.2.0]heptan-2-one, (1S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Oxabicyclo[3.2.0]heptan-2-one, (1S)-(75658-85-4)
• EPA Substance Registry System: 3-Oxabicyclo[3.2.0]heptan-2-one, (1S)-(75658-85-4)

Safety Data

• Hazardous Substances Data: 75658-85-4(Hazardous Substances Data)

Upstream product

• 4462-96-8 cis-1,2-cyclobutane dicarboxylic anhydride 
• 76186-04-4 (S)-4-isopropylthiazolidine-2-thione 
• 4462-96-8 3-oxabicyclo[3.2.0]heptane-2,4-dione 

Downstream Products

• 134877-12-6 (+)-(1S,2R)-1-carbomethoxy-2-methylcyclobutane 
• 55659-54-6 (-)-(1R,2R)-1,2-bis(hydroxymethyl)cyclobutane 

Relevant articles and documents

Enantioselective reduction of meso-cyclic-1,2-dicarboxylic anhydrides and 1,2-dicarboximides: Asymmetric synthesis of bicyclic lactones and hydroxylactams

Chiral bicyclic lactones (3,8,9) and bicyclic hydroxylactams (10-13) were synthesized by highly enantioselective reduction of meso-cyclic-1,2- dicarboxylic anhydrides (1, 4) and meso-cyclic-1,2-dicarboximides (2) with lithium aluminum hydride (LiAlH4)-alcohol(ROH)-(R)- or (S)-1,1'-bi-2- naphthol complex [(R)- or (S)-BINAL-H(ROH)]. Treatment of the hydroxylactams (10-13) with triethylsilane (Et3SiH) and trifluoroacetic acid (CF3CO2H) gave chiral bicyclic lactams (14, 15) in quantitative yields. Removal of the N-4-methoxyphenyl group of the lactams (14, 15) with cerium(IV) ammonium nitrate (CAN) proceeded smoothly to give the corresponding N-unsubstituted lactams (16, 17) in high optical purity.

AN ASYMMETRIC SYNTHESIS OF BICYCLIC LACTONES AND ITS APPLICATION TO THE ASYMMETRIC SYNTHESIS OF (1R,3S)-CIS-CHRYSANTHEMIC ACID

Optically active bicyclic lactones are synthesized from imides, derived from (R)-(-)-2-amino-2-phenylethanol and meso-cyclic-1,2-cis-dicarboxylic acids, by successive treatment with sodium bis(2-methoxyethoxy)aluminum hydride and sodium borohydride, followed by acid hydrolysis.This reaction is successfully applied to the asymmetric synthesis of (1R,3S)-cis-chrysanthemic acid.