Diastereoselective approach to an HIV protease inhibitor intermediate using a cation-exchange resin mediated Mannich-type reaction

Heterocycles

Volumn 73, Issue C, 2007, Pages 191-195

  Shimizu, Makoto ^a   Hayashi, Yukinori ^a   Hamanaka, Ryosuke ^a   Hachiya, Iwao ^a  

^a MIE UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 45249086575     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-07-S(U)25     Document Type: Article

References (22)

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19. 3) δ : -5.5, -5.0, 18.4, 25.8, 55.4, 59.0, 59.5, 63.9, 72.7, 73.4, 75.0, 77.5, 79.5, 110.2, 113.8, 119.4, 126.7, 127.7, 128.2, 131.4, 140.2, 156.0, 167.3.
20. Although the ketene t-butyldimethylsilyl acetal derived from methyl benzyloxyacetate could be used for the initial Mannich type reaction with the imine (1), the subsequent cyclization into β-lactam was not facile as in the case with the TBS derivative (2), and therefore, replacement of the TBS group was conducted in the present synthesis (Scheme 3).
21. 3) δ: 35.4, 52.7, 53.3, 72.0, 126.8, 126.9, 128.5, 128.6, 129.4, 131.7, 134.0, 136.8, 167.4, 173.0.
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