Research Topics
| Jonathan T ReevesSummaryAffiliation: Boehringer Ingelheim Publications
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Detail Information
Publications
Direct titanium-mediated conversion of ketones into enamides with ammonia and acetic anhydrideJonathan T Reeves
Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc Ridgefield, CT 06877 USA
Angew Chem Int Ed Engl 51:1400-4. 2012..The addition of edte (N,N,N',N'-tetrakis(2-hydroxyethyl)ethylenediamine) prior to workup enables water solubilization of Ti alkoxides and allows a simple extractive workup...- Copper-catalyzed annulation of 2-formylazoles with o-aminoiodoarenesJonathan T Reeves
Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc, 900 Old Ridgebury Road, P O Box 368, Ridgefield, Connecticut 06877 0368, USA
J Org Chem 75:992-4. 2010..The reaction also works for annulation of 2-formylindoles, 2-formylimidazole, 2-formylbenzimidazole, and a 3-formylpyrazole... - Room temperature palladium-catalyzed cross coupling of aryltrimethylammonium triflates with aryl Grignard reagentsJonathan T Reeves
Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc, 900 Ridgebury Road, P O Box 368, Ridgefield, Connecticut 06877 0368, USA
Org Lett 12:4388-91. 2010..Competition experiments established the reactivity of PhNMe(3)OTf relative to PhCl, PhBr, PhI, and PhOTf... - Trifluoromethyl ketones from enolizable carboxylic acids via enediolate trifluoroacetylation/decarboxylationJonathan T Reeves
Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc, 900 Old Ridgebury Road, P O Box 368, Ridgefield, Connecticut 06877 0368, USA
J Org Chem 73:9476-8. 2008..The process may be performed at -20 degrees C with a slight reduction in yield. The reaction was extended to the preparation of pentafluoroethyl and chlorodifluoromethyl ketones... - Zinc catalyzed and mediated propargylations with propargyl boronatesDaniel R Fandrick
Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc, 900 Old Ridgebury Road P O Box 368, Ridgefield, Connecticut 06877 0368, USA
Org Lett 12:88-91. 2010..The propargylation with crystalline and air-stable propargyl diethanolamine boronates was also achieved. A catalytic cycle is proposed, and preliminary mechanistic studies are discussed... - Mild and general zinc-alkoxide-catalyzed allylations of ketones with allyl pinacol boronatesKeith R Fandrick
Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc, 900 Ridgebury Road, P O Box 368, Ridgefield, Connecticut 06877 0368, USA
Org Lett 12:3748-51. 2010..The methodology is effective with 2 mol % of catalyst and with relatively short reaction times. Studies of the key exchange process are presented, which support a cyclic transition state for the boron to zinc exchange... - N-heterocyclic carbene-catalyzed Mukaiyama aldol reactionsJinhua J Song
Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc, 900 Old Ridgebury Road P O Box 368, Ridgefield, CT 06877 0368, USA
Org Lett 9:1013-6. 2007..These conditions are extremely mild and operationally simple and tolerate various functional groups. [reaction: see text].. - Copper catalyzed asymmetric propargylation of aldehydesDaniel R Fandrick
Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc, 900 Ridgebury Road P O Box 368, Ridgefield, Connecticut 06877 0368, USA
J Am Chem Soc 132:7600-1. 2010..The utility of the TMS homopropargylic alcohols was demonstrated by the facile conversion to a chiral dihydropyranone... - A general copper-BINAP-catalyzed asymmetric propargylation of ketones with propargyl boronatesKeith R Fandrick
Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc, 900 Ridgebury Road P O Box 368, Ridgefield, Connecticut 06877 0368, USA
J Am Chem Soc 133:10332-5. 2011..The resulting homopropargyl adducts are versatile latent carbonyls from which ?-butyrolactones, ?-hydroxy methyl ketones, and ?-hydroxycarboxylates are readily obtained... - N-heterocyclic carbene-catalyzed silyl enol ether formationJinhua J Song
Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc, 900 Old Ridgebury Road P O Box 368, Ridgefield, Connecticut 06877 0368, USA
Org Lett 10:877-80. 2008..In the presence of a catalytic amount of NHC 3 (IAd, 0.1 to 5 mol %), a series of enolizable ketones as well as cyclohexanecarboxaldehyde were efficiently converted into the corresponding silyl enol ethers at 23 degrees C in THF... - Highly diastereoselective zinc-catalyzed propargylation of tert-butanesulfinyl iminesDaniel R Fandrick
Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc, 900 Old Ridgebury Road P O Box 368, Ridgefield, Connecticut 06877 0368, USA
Org Lett 12:748-51. 2010..8:0.2 dr, respectively. The utility of the homopropargylic amines was demonstrated by the application to the synthesis of a cis-substituted pyrido-indole through a diastereoselective Pictet-Spengler cyclization... - Regioselective allene synthesis and propargylations with propargyl diethanolamine boronatesDaniel R Fandrick
Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc, 900 Old Ridgebury Road, P O Box 368, Ridgefield, Connecticut 06877 0368, USA
Org Lett 11:5458-61. 2009..Alternatively, the propargylation of aldehydes was achieved with use of the in situ generated lithiated complex... - Organometallic methods for the synthesis and functionalization of azaindolesJinhua J Song
Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc, 900 Old Ridgebury Road P O Box 368, Ridgefield, CT 06877 0368, USA
Chem Soc Rev 36:1120-32. 2007..In this tutorial review, we have surveyed the recent development of organometallic chemistry-based methods for azaindole synthesis... - A general synthesis of substituted formylpyrroles from ketones and 4-formyloxazoleJonathan T Reeves
Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc, Ridgefield, CT 06877 0368, USA
Org Lett 9:1875-8. 2007..The methodology was extended to an N-benzyl thiazolium salt... - Practical stereoselective synthesis of an alpha-trifluoromethyl-alpha-alkyl epoxide via a diastereoselective trifluoromethylation reactionJinhua J Song
Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc, 900 Old Ridgebury Road P O Box 368, Ridgefield, Connecticut 06877 0368, USA
J Org Chem 72:292-4. 2007..The fluoride-initiated CF3 addition to chiral keto ester 6a proceeded with a diastereoselectivity up to 86:14. The major diastereomer was readily obtained with a >99.5:0.5 dr through a simple crystallization of the crude product mixture... - Activation of TMSCN by N-heterocyclic carbenes for facile cyanosilylation of carbonyl compoundsJinhua J Song
Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc, 900 Old Ridgebury Road, P O Box 368, Ridgefield, CT 06877 0368, USA
J Org Chem 71:1273-6. 2006..01-0.5 mol % of N-heterocyclic carbene (1), leading to a range of trimethylsilylated cyanohydrins in very good to excellent yields. These conditions are extremely mild and simple and tolerate various functional groups... - A concise synthesis of butylcycloheptylprodigiosinJonathan T Reeves
Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc, Ridgefield, CT 06877, USA
Org Lett 9:1879-81. 2007..A short and efficient total synthesis of the tripyrrole alkaloid butylcycloheptylprodigiosin is described. Key to the brevity of the approach is a two-step synthesis of macrocyclic formylpyrrole 4 from cyclononenone 6... - Asymmetric synthesis of active pharmaceutical ingredientsVittorio Farina
Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc, 900 Ridgebury Road, Ridgefield, Connecticut 06877, USA
Chem Rev 106:2734-93. 2006