Stereocontrolled Transformations of trans α,β‐Aziridine Aldehydes toward Different Amino Hydroxylated Structures

References

• Bergmeier , S. C. 2000 . The synthesis of vicinal amino alcohols . Tetrahedron , 56 : 2561 – 2576 . and references cited herein
   Web of Science ®Google Scholar
• Bonini , C. , Righi , G. and D'Achille , R. 1996 . Regioselective opening of 3‐substituted N‐ethoxycarbonyl aziridine‐2‐carboxylates with metal halides toward the preparation of α and β‐aminoacids . Tetrahedron Lett. , 37 : 6893 – 6896 .
   Google Scholar
• Bonini , C. , Righi , G. and Franchini , T. 1998 . Highly regioselective opening of 3‐substituted N‐Boc‐2,3‐aziridino alcohol derivatives with metal halide . Tetrahedron Lett. , 39 : 2385 – 2388 .
   Google Scholar
• Righi , G. and Bonini , C. 2000 . “ Functionalised epoxides and aziridines: Reactivity with metal halides and synthetic applications,” . In Target in Heterocyclic Systems Edited by: Attanasi , O. A. and Spinelli , D. Vol. 4 , 139 – 165 . Italian Society of Chemistry .
   Google Scholar
• Hwang , G.‐I. , Chung , J.‐H. and Lee , W. K. 1996 . Efficient synthesis of Ephedra alkaloid analogues using an enantiomerically pure N‐[(R)‐(+)‐α‐methylbenzyl]aziridine‐2‐carboxaldehyde . J. Org. Chem. , 61 : 6183 – 6188 .
   PubMed Web of Science ®Google Scholar
• Andres , J. M. , de Elena , N. , Pedrosa , R. and Prez‐Encabo , A. 1999 . Efficient synthesis of syn‐aziridino alcohols by chelation‐controlled addition of dialkylzincs and Grignard reagents to N‐benzylaziridino aldehydes . Tetrahedron , 55 : 14137 – 14144 .
   Google Scholar
• Righi , G. , Pietrantonio , S. and Bonini , C. 2001 . Stereocontrolled “one pot” organometallic addition‐ring opening reaction of α,β‐aziridine aldehydes. A new entry to syn 1,2‐amino alcohols . Tetrahedron , 57 : 10039 – 10046 .
   Web of Science ®Google Scholar
• Righi , G. and Ciambrone , S. 2004 . Stereocontrolled addition of boron enolates to trans α,β‐aziridine aldehydes. A new route to anti 1,2‐aminoalcohols . Tetrahedron Lett. , 45 : 2103 – 2106 .
   Google Scholar
• Kolb , H. C. and Sharpless , K. B. 1998 . Transition Metals for Organic Synthesis Edited by: Beller , M. and Bolm , C. 243 New York : Wiley‐VCH .
   Google Scholar
• O'Brien , P. 1999 . Sharpless asymmetric aminohydroxylation: Scope, limitations and use in synthesis . Angew. Chem., Int. Ed. Engl. , 38 : 326 – 329 .
   PubMed Web of Science ®Google Scholar
• Hashimoto , N. , Fujioka , T. , Toyoda , T. , Muranushi , N. and Hirano , K. 1994 . Renin inhibitor: Transport mechanism in rat small intestinal brush‐border membrane vesicles . Pharm. Res. , 11 : 1448 – 1451 .
   PubMed Web of Science ®Google Scholar
• Yamada , Y. , Ando , K. , Ikemoto , Y. , Tada , H. , Shirakawa , E. , Inagaki , E. , Shibata , S. , Nakamura , I. , Hayashi , Y. , Ikegami , K. and Uchida , I. 1997 . Novel renin inhibitors containing (2S,3S,5S)‐2‐amino‐1‐cyclohexyl‐6‐methyl‐3,5‐heptanediol fragment as a transition‐state mimic at the P1‐P1′ cleavage site . Chem. Pharm. Bull. , 45 : 1631 – 1641 .
   PubMed Web of Science ®Google Scholar
• Okue , M. , Watanabe , H. , Kasahara , K. , Yoshida , M. , Horinouchi , S. and Kitahara , T. 2002 . Short‐step syntheses of all stereoisomers of preussin and their bioactivities . Biosci. Biotech. Biochem. , 66 : 1093 – 1096 .
   PubMed Web of Science ®Google Scholar
• Okue , M. , Watanabe , H. and Kitahara , T. 2001 . A concise synthesis of (+)‐preussin . Tetrahedron , 57 : 4107 – 4110 .
   Google Scholar
• Evans , D. A. and Chapman , K. T. 1986 . The directed reduction of β‐hydroxy ketones employing (AcO)3BHNMe4 . Tetrahedron Lett. , 27 : 5939 – 5942 .
   Web of Science ®Google Scholar
• Chen , K. , Gunderson , K. G. , Hardtmann , G. E. , Prasad , K. , Repic , O. and Shapiro , M. J. 1987 . A novel method for the in situ generation of alkoxydialkylboranes and their use in the selective preparation of 1,3‐syn diols . Chem. Lett. , : 1923 – 1926 .
   Google Scholar
• Tomaselli , A. G. and Heinrikson , R. L. 2000 . Targeting the HIV‐protease in AIDS therapy: A current clinical perspective . Biochim. Biophys. Acta , 1477 : 189 – 214 .
   PubMed Web of Science ®Google Scholar
• Chadrasekhar , S. , Mohapatra , S. and Yadav , J. S. 1999 . Practical synthesis of Abbott amino‐diol: A core unit of the potent renin inhibitor Zankiren . Tetrahedron , 55 : 4763 – 4768 .
   Google Scholar