Preparation of 2,3-trans-substituted piperidines from optically active β-amino-α-methylene esters: Synthesis of optically active (2S,3R)-(−)-epi-CP-99,994

Kamimura, Akio; Yo, Ryuichiro; Uno, Hidemitsu

doi:10.1016/j.tet.2017.06.054

Cited by 3 publications

(1 citation statement)

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“…The ammonolysis of lactone 5k afforded the corresponding hydroxyl amide that could go through Hofmann rearrangement and cyclization to yield chiral hydrazinated 1,3-oxazinan-2-one 10 in good yield (Scheme c) . Furthermore, aminated chiral piperidine 12 , the precursor of potent orexin receptor antagonist 2-Epi-CP-99,994, could be prepared via a N–N bond cleavage–deprotection–reductive amination sequence from hydrazinated piperidine 5r (Scheme d). It is worth mentioning that the enantioselectivities of the transformations mentioned above did not erode apparently.…”

Section: Resultsmentioning

confidence: 99%

Catalytic Enantioselective Aminative Difunctionalization of Alkenes

Huang,

Luo,

Liao

et al. 2024

J. Am. Chem. Soc.

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Enantioselective difunctionalization of alkenes offers a straightforward means for the rapid construction of enantioenriched complex molecules. Despite the tremendous efforts devoted to this field, enantioselective aminative difunctionalization remains a challenge, particularly through an electrophilic addition fashion. Herein, we report an unprecedented approach for the enantioselective aminative difunctionalization of alkenes via copper-catalyzed electrophilic addition with external azo compounds as nitrogen sources. A series of valuable cyclic hydrazine derivatives via either [3 + 2] cycloaddition or intramolecular cyclization have been achieved in high chemo-, regio-, enantio-, and diastereoselectivities. In this transformation, a wide range of functional groups, such as carboxylic acid, hydroxy, amide, sulfonamide, and aryl groups, could serve as nucleophiles. Importantly, a new cyano oxazoline chiral ligand was found to play a crucial role in the control of enantioselectivity.

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Section: Resultsmentioning

confidence: 99%