142096-79-5

Basic information

• Product Name: (+)-(1S,2S)-2-(2-phenylethyl)cyclopropylmethanol
• Synonyms: (+)-(1S,2S)-2-(2-phenylethyl)cyclopropylmethanol
• CAS NO: 142096-79-5
• Molecular Weight: 176.258
• Mol File: 142096-79-5.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: (+)-(1S,2S)-2-(2-phenylethyl)cyclopropylmethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(1S,2S)-2-(2-phenylethyl)cyclopropylmethanol(142096-79-5)
• EPA Substance Registry System: (+)-(1S,2S)-2-(2-phenylethyl)cyclopropylmethanol(142096-79-5)

Safety Data

• Hazardous Substances Data: 142096-79-5(Hazardous Substances Data)

Upstream product

• 75-11-6 diiodomethane 
• 75553-23-0 (E)-5-phenyl-2-penten-1-ol 
• 14399-53-2 bis(iodomethyl)zinc 
• 104-53-0 3-phenyl-propionaldehyde 
• 122-97-4 3-Phenyl-1-propanol 
• 33046-84-3 (2E)-5-phenyl-2-pentenal 
• 55282-95-6 ethyl (2E)-5-phenylpent-2-enoate 
• 167482-48-6 1,2-O-Isopropylidene-3-O-(p-phenylbenzyl)-4,5-O-<(1'R)-trans-5'-phenyl-2'-penten-1'-yl>-β-D-fructopyranose 
• 167482-59-9 trans-5-Phenyl-2-penten-1-al diethyl acetal 

Relevant articles and documents

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.

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.

Catalytic asymmetric cyclopropanation of allylic alcohols with titanium-TADDOLate: Scope of the cyclopropanation reaction

A substoichiometric amount of titanium-TADDOLate complex was effective at catalyzing the cyclopropanation reaction of allylic alcohols in the presence 1 equiv of bis(iodomethyl) zinc. After initial optimization of the catalyst structure, excellent yields and enantiomeric ratios were obtained for 3-aryl- or 3-heteroaryl-substituted allylic alcohols (up to 97:3). Alkyl-substituted allylic alcohols gave modest yields and enantiomeric ratios (up to 87:13) but these compare favorably with those observed with other substoichiometric chiral ligands. The full synthetic scope of the reaction is presented in this paper.