2H-azirine 3-phosphonates: A new class of chiral iminodienophiles. Asymmetric synthesis of quaternary piperidine phosphonates

Organic Letters

Volumn 4, Issue 4, 2002, Pages 655-658

  Davis, Franklin A ^a   Wu, Yongzhong ^a   Yan, Hongxing ^a   Prasad, Kavirayani R ^a   McCoull, William ^a  

^a Temple University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRINE DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; PHOSPHONIC ACID DERIVATIVE; PIPERIDINE DERIVATIVE;

ARTICLE; CHEMISTRY; CYCLIZATION; HYDROGENATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION REDUCTION REACTION; STEREOISOMERISM;

AZIRINES; CYCLIZATION; HYDROGENATION; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION-REDUCTION; PHOSPHONIC ACIDS; PIPERIDINES; STEREOISOMERISM;

EID: 0037149045     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol017289p     Document Type: Article

References (26)

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17. We have found it easier to work with dimethyl phosphonate analogues of aziridine phosphonates rather than the diethyl derivatives 3. Not only is the diastereoselectivity for the addition of the dimethyl chloromethylphosphonate anion to the sulfinimine better (dr 72:28 (other isomers) vs 59:41 for 3) but the products are more easily separated by chromatography and give simpler NMR spectra.
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