846044-72-2Relevant academic research and scientific papers
Concise enantioselective syntheses of (+)-L-733,060 and (2 S,3 S)-3-hydroxypipecolic acid by cobalt(III)(salen)-catalyzed two-stereocenter hydrolytic kinetic resolution of racemic azido epoxides
Devalankar, Dattatray A.,Chouthaiwale, Pandurang V.,Sudalai, Arumugam
supporting information, p. 102 - 104 (2014/01/06)
An efficient synthesis of the 2,3-disubstituted piperidines (+)-L-733,060 and (2S,3S)-3-hydroxypipecolic acid (≥99% ee) in high optical purity from commercially available starting materials is described. The strategy involves a cobalt-catalyzed hydrolytic
Kinetic resolution of secondary alcohols catalyzed by chiral phosphoric acids
Harada, Shingo,Kuwano, Satoru,Yamaoka, Yousuke,Yamada, Ken-Ichi,Takasu, Kiyosei
, p. 10227 - 10230 (2013/10/21)
Acid instead of base: Kinetic resolution of secondary alcohols is realized using chiral Bronsted acid catalyzed acylation instead of the conventional basic conditions. A broad range of functional groups are tolerated, such as aldehydes, carboxylic acids, and enoates. The selectivity factor (s) reaches up to 215 at ambient temperature. Copyright
Synthesis of (+)-L-733,060, (+)-CP-99,994 and (2S,3R)-3-hydroxypipecolic acid: Application of an organocatalytic direct vinylogous aldol reaction
Pansare, Sunil V.,Paul, Eldho K.
, p. 2119 - 2125 (2012/04/17)
The γ-butenolide obtained from an organocatalyzed, direct vinylogous aldol reaction of γ-crotonolactone and benzaldehyde serves as the key starting material in the expedient synthesis of a 3-hydroxy-2-phenyl piperidine intermediate which is converted to the target 2,3-disubstituted piperidines.
A stereoselective synthesis of (+)-L-733,060 from ethyl (R)-(+)-2,3-epoxypropanoate
Prevost, Sebastien,Phansavath, Phannarath,Haddad, Mansour
experimental part, p. 16 - 20 (2010/04/26)
An asymmetric synthesis of neurokinin substance P receptor antagonist (+)-L-733,060 starting from enantiomerically pure ethyl (R)-(+)-2,3-epoxypropanoate (ethyl glycidate) is described. The synthesis relies on a diastereoselective reductive amination, regioselective intramolecular epoxide opening, and in situ cyclization as the key steps.
A short enantioselective synthesis of (+)-L-733,060 via Shi epoxidation of a homoallylic carboxylate
Emmanuvel, Lourdusamy,Sudalai, Arumugam
, p. 5736 - 5738 (2008/12/22)
A short and efficient enantioselective synthesis of (+)-L-733,060 in 92% ee via Shi epoxidation of a homoallylic carboxylate is described. Johnson-Claisen rearrangement was employed to obtain the required carbon backbone, whilst intramolecular reductive O-to-N-ring expansion of a δ-azidolactone was used in the construction of the piperidine moiety.
Catalytic asymmetric vinylogous mannich reaction of W-(2-thienyl) sulfonylimines
Gonzalez, Alvaro Salvador,Arrayas, Ramon Gomez,Rivero, Marta Rodriguez,Carretero, Juan C.
supporting information; experimental part, p. 4335 - 4337 (2009/06/18)
(Chemical Equation Presented) Both cyclic and acyclic silyl dienol ethers participate efficiently in the asymmetric vinylogous Mannich reaction of N-2-thienylsulfonylimines catalyzed by copper(l) complexes of Fesulphos ligands. This procedure displays wid
Asymmetric synthesis of (+)-L-733,060
Yoon, Youn-Jung,Joo, Jae-Eun,Lee, Kee-Young,Kim, Yong-Hyun,Oh, Chang-Young,Ham, Won-Hun
, p. 739 - 741 (2007/10/03)
A concise, stereocontrolled synthesis of (+)-L-733,060 was achieved. Key features involve diastereoselective oxazoline formation catalyzed by palladium(0) and intramolecular cyclization by catalytic hydrogenation of an oxazoline.
