148701-46-6Relevant articles and documents
Iridium-catalyzed asymmetric allylic substitutions with bulky amines/oxidative double bond cleavage - Entry into the reetz synthesis of amino alcohols
Seehafer, Kai,Malakar, Chandi C.,Bender, Markus,Qu, Jianping,Liang, Chen,Helmchen, Günter
, p. 493 - 501 (2016/02/18)
Branched allylic amines were prepared by Ir-catalyzed enantioselective allylic aminations with the bulky N-nucleophiles HN(Boc)2 and HNBn2. The products were transformed into N-protected amino aldehydes, which were either reduced or coupled diastereoselectively with organometallic compounds to give vicinal amino alcohols. A formal synthesis of the neurokinin receptor antagonist (+)-L-733060 was carried out as an application. Ir-catalyzed enantioselective allylic aminations with bulky N-nucleophiles HN(Boc)2 and HNBn2 gave N-protected allylic amines, which were transformed into N-protected chiral amino aldehydes. These are useful chiral building blocks as previously demonstrated by Reetz et al. A formal synthesis of the neurokinin receptor antagonist (+)-L-733060 was carried out as an application.
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
, 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
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.
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.
Highly enantioselective synthesis of 3-hydroxy-2-phenylpiperidine via the sharpless AD-reaction
Stadler, Heinz,Boes, Michael
, p. 1067 - 1071 (2007/10/03)
Asymmetric dihydroxylation (AD) of the silyl enol ether (3) provided after hydrolysis the hydroxy ketone (4). Subsequent hydrogenation yielded the title compound (1) as a diastereomeric mixture. The cis-isomer is an important building block for the synthe
Stereoselective synthesis of (2S,3S)-3-hydroxy-2-phenylpiperidines, precursors of non-peptidic substance P antagonists
Calvez, Olivier,Langlois, Nicole
, p. 7099 - 7100 (2007/10/03)
(2S)-N-Boc-3-oxo-2-phenylpiperidine 5 and (2S,3S)-N-Boc-3-hydroxy-2- phenylpiperidine 6, known chiral building blocks for the synthesis of non- peptidic substance P antagonists, were prepared from erythro (2S)-N-benzyl 2- hydroxybenzylpyrrolidine derived from (S)-N-methoxy-N-methylpyroglutamide.
Azacyclic compounds compositions containing them and their use as tachykinin antagonists
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, (2008/06/13)
The present invention relates to compounds of formula (I), and salts and prodrugs thereof, wherein n is 1 , 2 or 3 and where any carbon atom of (CH2)n may be substituted by R4 and/or R5 ; X represents O or S; R
