57741-12-5Relevant articles and documents
One-Carbon Homologation of Primary Alcohols and the Reductive Homologation of Aldehydes Involving a Jocic-Type Reaction
Li, Zhexi,Gupta, Manoj K.,Snowden, Timothy S.
, p. 7009 - 7019 (2015/11/16)
(Trichloromethyl)carbinols, which are formed in one operation from either alcohols or aldehydes, can be converted into primary alcohols in a Jocic-type reaction involving LiBH4. The net result is a convenient two-step, one-carbon homologation of primary alcohols or a reductive one-carbon homologation of aldehydes featuring a broad substrate scope. The method is step-economical, and it nicely complements established one-carbon homologation strategies. (Trichloromethyl)carbinols, which are formed in one operation from either alcohols or aldehydes, can be converted into primary alcohols in a Jocic-type reaction involving LiBH4. The net result is a convenient two-step, one-carbon homologation of primary alcohols or a reductive one-carbon homologation of aldehydes featuring a broad substrate scope.
Trichloromethyl ketones: Asymmetric transfer hydrogenation and subsequent Jocic-type reactions with amines
Perryman, Michael S.,Harris, Matthew E.,Foster, Jade L.,Joshi, Anushka,Clarkson, Guy J.,Fox, David J.
supporting information, p. 10022 - 10024 (2013/10/22)
Amino-amides are important pharmaceutical building-blocks. The enantioselective reduction of trichloromethyl ketones using ruthenium transfer hydrogenation catalysts is reported. The products react in a range of Jocic-type reactions to give enantiomerically enriched amino-amides.
One-pot synthesis of trichloromethyl carbinols from primary alcohols
Gupta, Manoj K.,Li, Zhexi,Snowden, Timothy S.
experimental part, p. 4854 - 4860 (2012/07/30)
Versatile trichloromethyl carbinols can be prepared in one pot from primary alcohols by treatment with Dess-Martin periodinane (DMP) in CHCl3 followed by introduction of commercially available 1,5,7-triazabicyclo[4.4.0] dec-5-ene (TBD). A modification of the method was used to convert chiral primary alcohol (R)-(-)-2,2-dimethyl-1,3-dioxolane-4-methanol to the corresponding trichloromethyl carbinol with complete stereochemical fidelity, despite the reactant proceeding through a base-sensitive aldehyde intermediate.
One-pot in situ formation and reaction of trimethyl(trichloromethyl)silane: Application to the synthesis of 2,2,2-trichloromethylcarbinols
Henegar, Kevin E.,Lira, Ricardo
experimental part, p. 2999 - 3004 (2012/05/04)
2,2,2-Trichloromethylcarbinols are 1 are valuable synthetic intermediates with a multitude of uses. A scalable procedure for the synthesis of TMS-protected-2,2,2-trichloromethylcarbinols and 2,2,2-trichloromethylcarbinols 1 was developed that employs the in situ generation and reaction of trimethyl(trichloromethyl)silane (CCl3-TMS). The procedure avoids the exposure of the carbonyl compounds to the strongly basic conditions typically used for this transformation and also avoids isolation of the difficult-to-handle CCl3-TMS. This procedure was applied to diastereoselective trichloromethyl additions to 2-substituted 4-piperidinones and to reactions with a variety of structurally diverse aldehydes and ketones.
General and practical conversion of aldehydes to homologated carboxylic acids
Cafiero, Lauren R.,Snowden, Timothy S.
supporting information; experimental part, p. 3853 - 3856 (2009/07/01)
(Chemical Equation Presented) The reaction of aldehydes with trichloromethide followed by sodium borohydride or sodium phenylseleno(triethyl) borate under basic conditions affords homologated carboxylic acids in high yields. This operationally simple procedure provides a practical, efficient alternative to other homologation protocols. The approach is compatible with sensitive aldehydes including enals and enolizable aldehydes. It also offers convenient access to α-monodeuterated carboxylic acids.
Reeve's synthesis of 2-imino-4-thiazolidinone from alkyl (aryl) trichloromethylcarbinol revisited, a three-component process from aldehyde, chloroform and thiourea
Blanchet, Jér?me,Zhu, Jieping
, p. 4449 - 4452 (2007/10/03)
An efficient synthesis of 2-imino-4-thiazolidinones from readily accessible alkyl (aryl) trichloromethylcarbinols and thioureas under mild conditions is reported. A one-pot three-component synthesis of the title compounds from aldehyde, chloroform and thiourea is also developed for the first time
A new and practical synthesis of vinyl dichlorides via a non-Wittig-type approach
Wang, Zhe,Campagna, Silvio,Xu, Guoyou,Pierce, Michael E.,Fortunak, Joseph M.,Confalone, Pat N.
, p. 4007 - 4009 (2007/10/03)
A practical approach for the conversion of aldehydes to vinyl dichlorides has been developed. These are three-step, one-pot reactions involving the formation of trichlorocarbinol by treatment of aldehydes with trichloroacetic acid and sodium trichloroacetate followed by in situ protection and elimination reactions to form the desired vinyl dichlorides in 85 to 95% yields. (C) 2000 Dupont Pharmaceuticals Company.
A CATALYTIC ENANTIOSELECTIVE SYNTHESIS OF CHIRAL MONOSUBSTITUTED OXIRANES
Corey, E. J.,Helal, Christopher J.
, p. 5227 - 5230 (2007/10/02)
A new catalytic enentioselective synthesis of monosubstituted oxiranes has been developed from achiral trichloromethyl ketones by (a) enentioselective carbonyl reduction, (b) selective bis-dechlorination and (c) base-induced ring closure of the resulting chlorohydrins.
