764650-92-2Relevant academic research and scientific papers
Enantioselective total synthesis of (+)-arborescidine C and related tetracyclic indole alkaloids using organocatalysis
Sheth, Vishal M.,Hong, Bor-Cherng,Lee, Gene-Hsiang
, p. 3408 - 3412 (2017)
A concise and enantioselective synthesis of the tetracyclic indoles, including the naturally occurring compounds (+)-arborescidine C and (+)-arborescidine B, was achieved by the key step of Pictet-Spengler cyclization reaction with a Jacobsen-type thiourea organocatalyst. The synthetic process was further demonstrated in a pot-economy strategy and was achieved in a one-pot operation.
Regio-and enantioselective catalytic cyclization of pyrroles onto N-acyliminium lons
Raheem, Izzat T.,Thiara, Parvinder S.,Jacobsen, Eric N.
supporting information; experimental part, p. 1577 - 1580 (2009/04/07)
The regio- and enantioselective cyclization of pyrroles onto N-acyliminium ions generated in situ from hydroxylactams is reported. Modest to excellent ee's and yields are obtained in these novel Pictet-Spengler-type reactions with a chiral thiourea-pyrrole catalyst. Useful synthetic transformations of the versatile pyrroloindolizidinone and pyrroloquinolizidinone products are presented.
Organocatalytic asymmetric transfer hydrogenation of nitroolefins
Martin, Nolwenn J. A.,Ozores, Lidia,List, Benjamin
, p. 8976 - 8977 (2008/02/10)
We describe a highly efficient and highly enantioselective Hantzsch ester mediated conjugate transfer hydrogenation of β,β-disubstituted nitroolefins that is catalyzed by a Jacobsen-type thiourea catalyst. Copyright
Enantioselective Pictet-Spengler-type cyclizations of hydroxylactams: H-bond donor catalysis by anion binding
Raheem, Izzat T.,Thiara, Parvinder S.,Peterson, Emily A.,Jacobsen, Eric N.
, p. 13404 - 13405 (2008/09/16)
Highly enantioenriched indolizinone and quinolizinone products are obtained in the thiourea-catalyzed cyclization of tryptamine-derived hydroxylactams. Substituent and counterion effect studies point to a novel mechanism of catalysis involving rate-limiti
Enantioselective thiourea-catalyzed acyl-Mannich reactions of isoquinolines
Taylor, Mark S.,Tokunaga, Norihito,Jacobsen, Eric N.
, p. 6700 - 6704 (2007/10/03)
(Chemical Equation Presented) Inexpensive aromatic feedstocks are substrates for highly enantioselective acylative Mannich reactions catalyzed by a thiourea chiral hydrogen-bond donor 1. This methodology provides access to useful 1-substituted dihydroisoq
Highly enantioselective catalytic acyl-Pictet-Spengler reactions
Taylor, Mark S.,Jacobsen, Eric N.
, p. 10558 - 10559 (2007/10/03)
The enantioselective cyclization of N-acyliminium ions generated in situ from tryptamine is promoted with high enantioselectivity by a new chiral thiourea catalyst. This represents the first successful system for asymmetric catalysis of the Pictet-Spengle
