72739-14-1Relevant academic research and scientific papers
A practical synthesis of α-amino ketones via aryllithium addition to N-Boc-α-amino acids
Florjancic, Alan S.,Sheppard, George S.
, p. 1653 - 1656 (2003)
The reaction of N-Boc-α-amino acids with aryllithium reagents followed by removal of the nitrogen protecting group provides enantiomerically pure α-amino aryl ketones as their corresponding HCl salts. This practical two-step sequence gives rapid access to a pharmaceutically interesting class of compounds from commercially available starting materials.
Chiral Phosphoric Acid Catalyzed Enantioselective Synthesis of α-Tertiary Amino Ketones from Sulfonium Ylides
Guo, Wengang,Li, Pingfan,Luo, Yuzheng,Sun, Jianwei,Sung, Herman H.-Y.,Williams, Ian D.
, p. 14384 - 14390 (2020/09/15)
Herein we disclose a new catalytic asymmetric approach for the synthesis of chiral α-Amino ketones, which is particularly useful for the less accessible acyclic α-Tertiary cases. By a protonation-Amination sequence, our approach represents a rare asymmetric H-heteroatom bond insertion by α-carbonyl sulfonium ylides, an attractive surrogate of diazocarbonyls. The mild intermolecular C-N bond formation was catalyzed by chiral phosphoric acids with excellent efficiency and enantioselectivity. The products are precursors to other important chiral amine derivatives, including drug molecules and chiral ligands. The enantioselectivity was controlled by dynamic kinetic resolution in the amination step, rather than the initial protonation. This process opens up a new platform for the development of other related insertion reactions.
Rearrangement of N-tert-butanesulfinyl α-halo imines with alkoxides to N-tert-butanesulfinyl 2-amino acetals as precursors of N-protected and N-unprotected α-amino carbonyl compounds
Colpaert, Filip,Mangelinckx, Sven,Denolf, Bram,De Kimpe, Norbert
experimental part, p. 6023 - 6032 (2012/10/08)
Reaction of N-tert-butanesulfinyl α-halo imines with alkoxides afforded new N-tert-butanesulfinyl 2-amino acetals in good to excellent yield. These N-tert-butanesulfinyl 2-amino acetals are convenient precursors for the TMSOTf-promoted synthesis of the co
An efficient synthesis of both enantiomers of Cathinone by regioselective reductive ring opening of substituted aziridines
Hwang, Gweon Il,Chung, Jae-Ho,Lee, Won Koo
, p. 12111 - 12116 (2007/10/03)
Both enantiomers of Cathinone were prepared as HCl salts from N-(R)-α-methylbenzylaziridine-2(S)-carboxaldehyde 2c and its enantiomer N-(S)-α-methyl-benzylaziridine-2(R)-carboxaldehyde 3c in high yield. This process makes it possible to prepare other aromatic and heteroaromatic analogs of Cathinone efficiently.
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