Synergistic NaBH₄ Reduction/Cyclization of 2‐Aroylcyclopropane‐1‐carboxylates: Synthesis of 3‐Oxabicyclo[3.1.0]hexane Derivatives

Abstract

An NaBH4 reduction/cyclization reaction of readily available 2‐aroyl‐1‐cyano‐3‐arylcyclopropane‐1‐carboxylate compounds was investigated. The process results in the stereoselective synthesis of 3‐oxabicyclo[3.1.0]hexane derivatives in high yields.

Synthesis and copolymerization of novel oxy ring-substituted isopropyl cyanoarylacrylates

“…The ECAA was also used in N,N'-dioxide-lanthanum(III)catalyzed asymmetric cyclopropanation with 2-bromomalonates [5]. It was employed in DBU-mediated [4 + 2] annulations of donor-acceptor cyclopropanes [6], in synergistic NaBH4 reduction/cyclization in synthesis of 3-oxabicyclo[3.1.0]hexane derivatives [7], as well as in studies on synthetic access to pyrano [3,2-c] quinoline and 3-substituted quinoline derivatives [8]. Benzyloxy ring-substituted ECAA was used in synthesis and biological evaluation of arylidene-thiazolidinediones with potential hypoglycemic and hypolipidemic activities [9].…”

Synthesis and styrene copolymerization of novel phenoxy ring-substituted isopropyl phenylcyanoacrylates

“…This PCA was used also in N,N'-Dioxide-Lanthanum(III)-catalyzed asymmetric cyclopropanation of 2-cyano-3arylacrylates with 2-bromomalonates [3], in synthesis of substitiuted tetrazoles [4], and in synthesis of electrophilic TSEs using lipase as a biocatalyst [5]. 4-Phenoxy PCA was used in studies on quinolin-2(1H)-one derivatives [6], whereas 3-fluorophenoxy ring-substituted PCA was employed in synergistic reduction/cyclization of 2-aroylcyclopropane-1-carboxylates [7]. 2,6-Dimethoxy ring-substituted PCA was used in preparation of 2-cyanopropanoic acid, amide and ester derivatives as estrogen receptor selective NF-κB inhibitors for the treatment of sepsis [8] as well as in preparation of 2-cyanopropanoic acid amide and ester derivatives as estrogen receptor binding agents for use as antiinflammatory and immunomodulatory agents [9].…”