91230-16-9Relevant academic research and scientific papers
Photoredox/Cobalt Dual-Catalyzed Decarboxylative Elimination of Carboxylic Acids: Development and Mechanistic Insight
Cartwright, Kaitie C.,Joseph, Ebbin,Comadoll, Chelsea G.,Tunge, Jon A.
, p. 12454 - 12471 (2020/09/09)
Recently, dual-catalytic strategies towards the decarboxylative elimination of carboxylic acids have gained attention. Our lab previously reported a photoredox/cobaloxime dual catalytic method that allows the synthesis of enamides and enecarbamates directly from N-acyl amino acids and avoids the use of any stoichiometric reagents. Further development, detailed herein, has improved upon this transformation's utility and further experimentation has provided new insights into the reaction mechanism. These new developments and insights are anticipated to aid in the expansion of photoredox/cobalt dual-catalytic systems.
Inhibition of serine and proline racemases by substrate-product analogues
Harty, Matthew,Nagar, Mitesh,Atkinson, Logan,Legay, Christina M.,Derksen, Darren J.,Bearne, Stephen L.
, p. 390 - 393 (2015/06/01)
d-Amino acids can play important roles as specific biosynthetic building blocks required by organisms or act as regulatory molecules. Consequently, amino acid racemases that catalyze the formation of d-amino acids are potential therapeutic targets. Serine
Lewis basic selenium catalyzed chloroamidation of olefins using nitriles as the nucleophiles
Tay, Daniel Weiliang,Tsoi, Ivan Tan,Er, Jun Cheng,Leung, Gulice Yiu Chung,Yeung, Ying-Yeung
supporting information, p. 1310 - 1313 (2013/04/24)
A Lewis base catalyzed chloroamidation of olefinic substrates was achieved using diphenyl selenide as the catalyst. The reaction conditions are mild and suitable for a wide range of substrates including those which are acid labile.
Platinum-catalyzed direct amination of allylic alcohols with aqueous ammonia: Selective synthesis of primary allylamines
Das, Kalpataru,Shibuya, Ryozo,Nakahara, Yasuhito,Germain, Nicolas,Ohshima, Takashi,Mashima, Kazushi
supporting information; experimental part, p. 150 - 154 (2012/02/16)
Direct amination of unactivated allylic alcohols with aqueous ammonia was catalyzed by a Pt/phosphine complex to give the corresponding allylamines along with water as the sole by-product. Under optimized reaction conditions, primary allylamines were obtained as major products with excellent monoallylation selectivity. cod=1,5-cyclooctadiene.
Efficient synthesis of a 7-azabicyclo[2.2.1]heptane based GlyT1 uptake inhibitor
Xiong, Hui,Frietze, William,Andisik, Donald W.,Ernst, Glen E.,Palmer, William E.,Hinkley, Lindsay,Varnes, Jeffrey G.,Albert, Jeffrey S.,Veale, Chris A.
scheme or table, p. 6741 - 6744 (2011/02/25)
An efficient synthetic route based on generation and subsequent electrophilic reaction of a Boc-protected azabicyclo[2.2.1]heptane anion to prepare a potent GlyT1 uptake inhibitor (1) is described.
Chemo- and diastereoselective cyclopropanation of allylic amines and carbamates
Csatayová, Kristína,Davies, Stephen G.,Lee, James A.,Ling, Kenneth B.,Roberts, Paul M.,Russell, Angela J.,Thomson, James E.
, p. 8420 - 8440 (2010/12/20)
A highly chemo- and diastereoselective protocol for the cyclopropanation of tertiary allylic amines with Shi's carbenoid [CF3CO 2ZnCH2I] is described. The high levels of diastereoselectivity observed in these reactions may be attributed to chelation of the nitrogen atom to the zinc reagent, which then transfers a methylene unit to the syn-face of the olefin. Furthermore, a stereodivergent protocol for the cyclopropanation of a range of allylic carbamates has been developed, which provides access to both diastereoisomers of the corresponding cyclopropanes with very high levels of diastereoselectivity: cyclopropanation with the Wittig-Furukawa reagent [Zn(CH2I)2] proceeds under chelation control to give the corresponding syn-product, whilst reaction with Shi's carbenoid proceeds under steric control to give the corresponding anti-cyclopropane, in >95:5 dr in both cases.
The stereodivergent aziridination of allylic carbamates, amides and sulfonamides
Davies, Stephen G.,Ling, Kenneth B.,Roberts, Paul M.,Russell, Angela J.,Thomson, James E.,Woods, Philip A.
experimental part, p. 6806 - 6813 (2010/09/17)
A stereodivergent protocol for the aziridination of a range of cyclic allylic amine derivatives has been developed. syn-Products can be obtained in >99:1 dr under H-bonded control and anti-products are obtained in >99:1 dr under steric control by judiciou
cis- and trans-Stereoselective Epoxidation of N-Protected 2-Cyclohexen-1-ylamines
O'Brien, Peter,Childs, Amanda C.,Ensor, Gareth J.,Hill, Cheryl L.,Kirby, Jonathan P.,Dearden, Michael J.,Oxenford, Sally J.,Rosser, Clare M.
, p. 4955 - 4957 (2007/10/03)
(Equation Presented) The first systematic study of the cis and trans stereoselectivity in the m-CPBA epoxidation of N-protected cyclic allylic amines has been completed. Mono-N-protected systems gave epoxides with cis stereochemistry (amides are better ci
MITSUNOBU REACTIONS OF N-ALKYL AND N-ACYL SULFONAMIDES - AN EFFICIENT ROUTE TO PROTECTED AMINES
Henry, James R.,Marcin, Lawrence R.,McIntosh, Matthias C.,Scola, Paul M.,Harris, G. Davis,Weinreb, Steven M.
, p. 5709 - 5712 (2007/10/02)
N-Methyl p-toluenesulfonamide and N-BOC p-toluenesulfonamide can be directly coupled with primary or secundary alcohols under Mitsunobu conditions to afford various sulfonamide-protected amines.
Allylic Selenides in Organic Synthesis: New Methods for the Synthesis of Allylic Amines
Shea, Regan G.,Fitzner, Jeffrey N.,Fankhauser, John E.,Spaltenstein, Andreas,Carpino, Philip A.,et al.
, p. 5243 - 5252 (2007/10/02)
Oxidative rearrangement of allylic selenides in the presence of various amine nucleophiles provides synthetic access to a variety of allylic amine derivatives.The stereochemical outcome of these reactions has been investigated, and is consistent with a -sigmatropic rearrangement mechanism.Several D-α-amino acids and racemic β,γ-unsaturated α-amino acids were prepared in this manner.A variant of this process employing an achiral allylic selenide and chiral amide afforded protected allylic amines in low diastereoisomeric excess.
