Synthesis, reactivity and conformational stability of an l-phenylalanine derived oxadiazinanone

Dore, Delvis D.; Burgeson, James R.; Davis, Ryan A.; Hitchcock, Shawn R.

doi:10.1016/j.tetasy.2006.09.002

Cited by 9 publications

(1 citation statement)

References 19 publications

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“…We became interested in determining if it would be possible to prepare chiral oxadiazines from a variety of α‐amino acids. We had previously prepared hydrazine 19 from L ‐phenylalaninol [20] and sought to use this material to prepare a series of oxadiazines (Scheme ). Thus, hydrazine 19 was acylated at nitrogen using either propanoyl chloride, benzoyl chloride, or 1‐naphthoyl chloride to afford the corresponding hydrazides 20a , 20b , 20c , respectively.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and X‐ray crystal structures of chiral, nonracemic 5,6‐dihydro‐4H‐1,3,4‐oxadiazines

Hitchcock

Dean

Kelley

et al. 2010

Journal of Heterocyclic Chem

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A series of chiral, nonracemic oxadiazines have been prepared from (1R,2S)-ephedrine, (1R,2S)-norephedrine, and L-phenylalaninol. The synthesis of the Ephedra-based oxadiazines was accomplished by a process of N-nitrosation, reduction, acylation, and acid-catalyzed cyclization. The trans-and cis-diastereomeric oxadiazines derived from (1R,2S)-ephedrine were analyzed by 1 H NMR spectroscopy and by single crystal X-ray crystallographic analysis. The stereochemistry of the (1R,2S)-norephedrine-derived oxadiazines was assigned based on 1 H NMR spectroscopy and by analogy with the X-ray crystal structure of the (1R,2S)-ephedrine-based oxadiazines. In addition, L-phenylalaninol was used as a template to prepare a series of oxadiazines substituted at the N 4 -nitrogen with an isopropyl group. This was accomplished by a reductive alkylation of L-phenylalaninol with acetone and subsequent hydrazide formation. These hydrazides were reacted with methanesulfonyl chloride to yield the corresponding oxadiazines by a base-mediated cyclization.

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Section: Resultsmentioning

confidence: 99%

Synthesis and X‐ray crystal structures of chiral, nonracemic 5,6‐dihydro‐4H‐1,3,4‐oxadiazines

Hitchcock

Dean

Kelley

et al. 2010

Journal of Heterocyclic Chem

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Asymmetric Synthesis of Six‐Membered Ring Nitrogen Heterocycles with More Than One Heteroatom

Mátyus¹,

Tapolcsányi²

2009

Asymmetric Synthesis of Nitrogen Heterocycles

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Synthesis of Chiral 2‐Hydroxy‐1‐methylpropanoates by Rhodium‐Catalyzed Stereoselective Hydrogenation of α‐(Hydroxymethyl)‐acrylate Derivatives

et al. 2008

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Abstract:The synthesis of chiral 3-hydroxy-2-methylpropanoic acid esters (e.g., "Roche ester" 3a) based on the rhodium-catalyzed stereoselective hydrogenation of Baylis-Hillman reaction products was investigated. Full conversions and enantioselectivities of up to 99% at a substrate/catalyst ratio of up to 500/1 were achieved by application of bisphospholanes of the catASium M series as ancillary ligands. An interesting kinetic resolution was observed by the diastereoselective hydroxy-directed hydrogenation of related racemic b-branched precursors affording mainly anti-isomers with up to 96%ee.

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Synthesis, reactivity and conformational stability of an l-phenylalanine derived oxadiazinanone

Cited by 9 publications

References 19 publications

Synthesis and X‐ray crystal structures of chiral, nonracemic 5,6‐dihydro‐4H‐1,3,4‐oxadiazines

Synthesis and X‐ray crystal structures of chiral, nonracemic 5,6‐dihydro‐4H‐1,3,4‐oxadiazines

Asymmetric Synthesis of Six‐Membered Ring Nitrogen Heterocycles with More Than One Heteroatom

Synthesis of Chiral 2‐Hydroxy‐1‐methylpropanoates by Rhodium‐Catalyzed Stereoselective Hydrogenation of α‐(Hydroxymethyl)‐acrylate Derivatives

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