173239-49-1

Upstream product

• 75-11-6 diiodomethane 
• 142096-78-4 (E)-1-hydroxy-4-(triphenylmethoxy)-2-butene 
• 409307-02-4 (1S,5R)-2-oxo-1-phenylsulfonyl-3-oxabicyclo[3.1.0]hexane 
• 1449741-24-5 (1S,2R)-2-(triphenylmethoxy)methyl-1-(N-methoxy-N-methyl)carbamoyl-1-phenylsulfonylcyclopropane 
• 1449741-25-6 (1S,2S)-2-(triphenylmethoxymethyl)-1-(N-methoxy-N-methyl)carbamoylcycropropane 
• 76-83-5 trityl chloride 

Downstream Products

• 53187-82-9 (trans-cyclopropane-1,2-diyl)dimethanol 
• 167255-48-3 ((1R,2R)-2-Hydroxymethyl-cyclopropylmethyl)-carbamic acid tert-butyl ester 
• 1638768-80-5 (1S,2S)-1-[[(N-tert-butoxycarbonyl)amino]methyl]-carboxycyclopropane 
• 188186-32-5 ((1R,2S,1'R,2'S)-2'-Trityloxymethyl-bicyclopropyl-2-yl)-methanol 

Relevant academic research and scientific papers

Chiral recyclable fluorous disulfonamide ligand for catalytic enantioselective cyclopropanation of allylic alcohols

Allylic alcohols reacted with Et2Zn and CH2I2 in the presence of a catalytic amount of fluorous disulfonamide 3a to afford the corresponding cyclopropylmethanols in 69%-quantitative yields with 49-85% ee. Recovery of the fluorous ligand 3a was readily performed from the reaction mixture by the fluorous solid-phase extraction (FSPE), and the recovered 3a could be reused without a significant loss of the catalytic activity and enantioselectivity.

Cyclopropane-based conformational restriction of GABA by a stereochemical diversity-oriented strategy: Identification of an efficient lead for potent inhibitors of GABA transports

A series of cyclopropane-based conformationally restricted γ-aminobutyric acid (GABA) analogs with stereochemical diversity, that is, the trans- and cis-2,3-methano analogs Ia and Ib and their enantiomers ent-Ia and ent-Ib, and also the trans- and cis-3,4

Catalytic enantioselective cyclopropanation of allylic alcohols using recyclable fluorous disulfonamide ligand

Cyclopropanation of allylic alcohols with Et2Zn and CH2I2 in the presence of a catalytic amount of fluorous disulfonamide 3 afforded the corresponding cyclopropylmethanols in 69-96% yield with 49-83% ee. The fluorous ligand 3 was readily recovered from the reaction mixture by the fluorous solid-phase extraction (FSPE) and could be reused without a significant loss of the catalytic activity and enantioselectivity.

Asymmetric Simmons-Smith reaction of allylic alcohols with Al Lewis acid/N Lewis base bifunctional Al(salalen) catalyst

(Chemical Presented) Three angles: A highly enantioselective Simmons-Smith reaction of trans-disubstituted allylic alcohols was achieved by using a catalytic amount of an Al(salalen) complex at room temperature (see scheme).

N,N,N′,N′-Tetraalkyl-2,2′-dihydroxy-1,1′- binaphthyl-3,3′-dicarboxamides: Novel Chiral Auxiliaries for Asymmetric Simons-Smith Cyclopropanation of Allylic Alcohols and for Asymmetric Diethylzinc Addition to Aldehydes

The newly introduced tittle compounds were found to be efficient chiral auxiliaries for the asymmetric Simmons-Smith cyclopropanation of allylic alcohols and for asymmetric addition of diethylzinc to aldehydes. For example, Simmons- Smith cyclopropanation of cinnamyl alcohol in the presence of N,N,N′,N′-tetraethyl-2,2′-dihydroxy-1, 1′-binaphthyl-3, 3′-dicarboxamide (1b) proceeded with high enantioselectivity of 94% ee and addition of diethylzinc to benzaldehyde in the presence of N,N,N′,N′-tetraisopropyl-2,2′-dihydroxy-1,1′-binaphthyl- 3,3′-dicarboxamide (1e) proceeded with enantioselectivity of 99% ee. Although the reaction mechanism of these reactions is still nuclear, a monomeric seven-membered 2,2′-dihydroxy-1,1′-binaphthyl-3,3′-dicarboxamide (1)-Zn complex is considered to be an active species which catalyzes the above reactions, on the basis of NMR experiments.

A new chiral disulfonamide ligand derived from α-amino acid for catalytic enantioselective cyclopropanation

A new disulfonamide prepared from α-amino acid in five steps catalyzed cyclopropanation of allylic alcohols with Et2Zn and CH2I2 to afford the corresponding cyclopropylmethanols in moderate to good enantioselectivites. In particular, the reaction of cinnamyl alcohol in the presence of a chiral disulfonamide 1k afforded an excellent enantioselectivity (85% ee).

A Catalytic Enantioselective Reaction Using a C2-Symmetric Disulfonamide as a Chiral Ligand: Simmons-Smith Cyclopropanation of Allylic Alcohols by the Et2Zn-CH2I2-Disulfonamide System

A catalytic and enantioselective Simmons-Smith cyclopropanation of an allylic alcohol was developed by the reaction of an allylic alcohol with Et2Zn and CH2I2 in the presence of a catalytic amount of chiral disulfonamide 4.

Asymmetric Simmons-Smith Cyclopropanation of E-Allylic Alcohols Using 1,1'-Bi-2-naphthol-3,3'-dicarboxamide as a Chiral Auxiliary

N,N,N',N'-Tetraethyl-1,1'-bi-naphthol-3,3'-dicarboxamide (1b) was found to be an effective chiral auxiliary for asymmetric Simmons-Smith cyclopropanation and high enantioselectivity greater than 85percent ee was achieved in the reaction of E-allylic alcohols.

Enantioselective Cyclopropanation of Allylic Alcohols Catalyzed by a Chiral Disulfonamide-Aluminum Complex

A chiral disulfonamide-alkylaluminum complex prepared from (1R,2R)-N,N'-bis(benzenesulfonyl)-1,2-cyclohexanediamine and trialkylaluminum or i-Bu2AlH has been found to catalyze a Simmons-Smith cyclopropanation of allylic alcohols with Et2Zn and CH2I2 to afford the corresponding cyclopropanes in excellent yields with high enantiomeric excesses.

A catalytic enantioselective reaction using a C2-symmetric disulfonamide as a chiral ligand: Cyclopropanation of allylic alcohols by the Et2Zn-CH2I2-disulfonamide system

The first catalytic, enantioselective Simmons-Smith cyclopropanation of an allylic alcohol has been achieved by the reaction of an allylic alcohol with Et2Zn and CH2I2 in the presence of a catalytic amount of chiral disulfonamide 1.