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Di Simone, B.; Savoia, D.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron: Asymmetry 1995, 6, 301. For a related asymmetric reduction using cis-l-amino-2-indanol see: Hong, Y.; Gao, Y; Nie, X.; Zepp, C. M. Tetrahedron Lett. 1994, 35, 6631.
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Di Simone, B.; Savoia, D.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron: Asymmetry 1995, 6, 301. For a related asymmetric reduction using cis-l-amino-2-indanol see: Hong, Y.; Gao, Y; Nie, X.; Zepp, C. M. Tetrahedron Lett. 1994, 35, 6631.
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0343001408
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(1S,2R)-and (lR,2S)-l-amino-2-indanols are commercially available from Aldrich and Sepracor
-
(1S,2R)-and (lR,2S)-l-amino-2-indanols are commercially available from Aldrich and Sepracor.
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13
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0001405437
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Eds. Abel, E. W.; Stone, F. G. A.; Wilkinson, G.; Pergamon: New York. Chapter 11.1
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b) Jacobsen, E. N.; Zhang, W.; Muci, A. R.; Ecker, J. R.; Deng, L. J. Am. Chem. Soc. 1991,113, 7063. The procedure for the synthesis on large scale of l-amino-2-indanol which uses in the key step the Jacobsen's epoxidation of indene is reported by Davies, I. W.; Reider, P. J. Chem. Ind. 1996, 412.
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a) Senanayake, C. H.; Roberts, E. F.; DiMichele, L.; Ryan, K. M.; Liu, J.; Fredenburg, L. E.; Foster, B. S.; Douglas, A. W.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1995. 36, 3993.
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Foster, B.S.7
Douglas, A.W.8
Larsen, R.D.9
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Reider, P.J.11
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b) Senanayake, C. H.; DiMichele, L.; Liu, J.; Fredenburg, L. E.; Ryan, K. M.; Roberts, E. F.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1995, 36, 7615.
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0342567024
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note
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2: MeOH 95:5). The HPLC analysis was performed with a Chiralcel ODH column. Ee 99.5%. The Chromatographic analysis was performed with a gradient technique (hexane:isopropanol 90:10 from hexane isopropanol 40:60 in 30 minutes) with a flow rate of 0.5 mL/min. (S,R)-(+)-(5) tR=11.72(min); (R,S)-(-)-(5) tr=13.52(min).
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25
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33845282886
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a) Corey, E. J.; Bakshi, R. K.; Shibata, S. J. J. Am. Chem. Soc. 1987, 109, 5551.
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b) Corey, E. J.; Bakshi, R. K.; Shibata, S.; Chen, C.-P; Singh, V. K. J. Am. Chem. Soc. 1987, 109, 7925.
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Singh, V.K.5
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0026727019
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and ref. therein
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For quantum chemical modeling of the ketone-borane complex of oxaazaborolidine see: Nevalainen, V. Tetrahedron: Asymmetry 1992, 3, 1563, and ref. therein.
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