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Volumn 52, Issue 4, 1987, Pages 702-704

Asymmetric Reduction of Phosphinyl Imines with Hydride Reagents. Enantioselective Synthesis of Chiral Primary Amines

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EID: 0000992394     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00380a047     Document Type: Letter
Times cited : (33)

References (15)
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    • For reviews, see: Morrison, J. D., Academic: New York (b) Grandbois, E. R.; Howard, S. I.; Morrison, J. D. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: New York, 1983; Vol. 2, Chapter 3. (c) Haubenstock, H. Top. Stereochem. 1983, 14, 231. Recent additional studies include the following, (d) B-(3-pinanyl)-9-borabicyclo[3.3.1]nonane: Brown, H. C.; Pai, G. G. J. Org. Chem. 1985, 50, 1384 and cited references, (e) Diisopinocampheylchloroborane: Chandrasekhar an, J.; Ramachandran, P. V.; Brown, H. C. J. Org. Chem. 1985, 50, 5446; Brown, H. C.; Chandrasekharan, J.; Ramachandran, P. V. J. Org. Chem. 1986, 51, 3394. (f) K 9-0-DIPGF-9-BBNH: Brown, H. C.; Park, W. S.; Cho, B. T. J. Org. Chem. 1986, 51, 1984; Brown, H. C.; Cho, B. T.; Park, W. S. J. Org. Chem. 1986, 51, 3396. Other dialkylmonoalkoxyborohydrides, Brown, H. C.; Park, W. S.; Cho, B. T. J. Org. Chem. 1986, 51, 3278. (g) Chiral sulfamideS/LiAlH4: Hawkins, J. M.; Sharpless, K. B. J. Org. Chem. 1984, 49, 3861. (h) /3-Amino alcohols/BH3: Itsumo, S.; I to, K.; Hirao, A.; Nakahama, S. J. Org. Chem. 1984, 49, 1984 and cited references. (i) Polymeric (S)-prolinol/BHa: Itsumo, S.; Ito, K.; Hirao, A.; Nakahama, S. J. Chem. Soc., Perkin Trans. 1 1984, 2887.
    • For reviews, see: (a) Midland, M. M. Asymmetric Synthesis; Morrison, J. D., Academic: New York, 1983; Vol. 2, Chapter 2. (b) Grandbois, E. R.; Howard, S. I.; Morrison, J. D. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: New York, 1983; Vol. 2, Chapter 3. (c) Haubenstock, H. Top. Stereochem. 1983, 14, 231. Recent additional studies include the following, (d) B-(3-pinanyl)-9-borabicyclo[3.3.1]nonane: Brown, H. C.; Pai, G. G. J. Org. Chem. 1985, 50, 1384 and cited references, (e) Diisopinocampheylchloroborane: Chandrasekhar an, J.; Ramachandran, P. V.; Brown, H. C. J. Org. Chem. 1985, 50, 5446; Brown, H. C.; Chandrasekharan, J.; Ramachandran, P. V. J. Org. Chem. 1986, 51, 3394. (f) K 9-0-DIPGF-9-BBNH: Brown, H. C.; Park, W. S.; Cho, B. T. J. Org. Chem. 1986, 51, 1984; Brown, H. C.; Cho, B. T.; Park, W. S. J. Org. Chem. 1986, 51, 3396. Other dialkylmonoalkoxyborohydrides, Brown, H. C.; Park, W. S.; Cho, B. T. J. Org. Chem. 1986, 51, 3278. (g) Chiral sulfamideS/LiAlH4: Hawkins, J. M.; Sharpless, K. B. J. Org. Chem. 1984, 49, 3861. (h) /3-Amino alcohols/BH3: Itsumo, S.; I to, K.; Hirao, A.; Nakahama, S. J. Org. Chem. 1984, 49, 1984 and cited references. (i) Polymeric (S)-prolinol/BHa: Itsumo, S.; Ito, K.; Hirao, A.; Nakahama, S. J. Chem. Soc., Perkin Trans. 1 1984, 2887.
    • (1983) Asymmetric Synthesis , vol.2
    • Midland, M.M.1
  • 4
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    • Landor, S. R.; Chan, Y. M.; Sonola, 0. 0.; Tatchell, A. R. J. Chem. Soc., Perkin Trans. 1 Chem. Lett 1986
    • (a) Landor, S. R.; Sonola, O. O.; Tatchell, A. R. J. Chem. Soc., Perkin Trans. 1 1974, 1902; Landor, S. R.; Chan, Y. M.; Sonola, 0. 0.; Tatchell, A. R. J. Chem. Soc., Perkin Trans. 1 1984, 493. (b) Itsuno, S.; Nakano, M.; Ito, K.; Hirao, A.; Owa, M.; Kanda, N.; Nakahama, S. J. Chem. Soc., Perkin Trans. 1 1985, 2615. (c) Itsuno, S.; Tanaka, K.; Ito, K. Chem. Lett. 1986, 1133.
    • (1974) J. Chem. Soc., Perkin Trans. 1 , pp. 1902
    • Landor, S.R.1    Sonola, O.O.2    Tatchell, A.R.3
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    • (b) Krzyzanowska, B.; Stec, W. J. Synthesis 1982, 270.
    • (a) Krzyzanowska, B.; Stec, W. J. Synthesis 1978, 521. (b) Krzyzanowska, B.; Stec, W. J. Synthesis 1982, 270.
    • (1978) Synthesis , pp. 521
    • Krzyzanowska, B.1    Stec, W.J.2
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    • Wiley: New York (b) Kenner, G. W.; Moore, G. A.; Ramage, R. Tetrahedron Lett. 1976, 4005. (c) Koziara, A.; Olejniczak, B.; Osowska, K.; Zwierzak, A. Synthesis 1982, 918. (d) Cleavage of optically active N-(diphenylphosphinyl)amines with HC1 affords the corresponding amines with no loss of optical purity.
    • Greene, T. W. Protective Groups in Organic Synthesis; Wiley: New York, 1981; pp 281–282. (b) Kenner, G. W.; Moore, G. A.; Ramage, R. Tetrahedron Lett. 1976, 4005. (c) Koziara, A.; Olejniczak, B.; Osowska, K.; Zwierzak, A. Synthesis 1982, 918. (d) Cleavage of optically active N-(diphenylphosphinyl)amines with HC1 affords the corresponding amines with no loss of optical purity.
    • (1981) Protective Groups in Organic Synthesis , pp. 281-282
    • Greene, T.W.1
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    • (b) Noyori, R.; Tomino, I.; Yamada, M. ; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6717.
    • (a) Noyori, R.; Tomino, I.; Tanimoto, Y.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6709. (b) Noyori, R.; Tomino, I.; Yamada, M.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6717.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 6709
    • Noyori, R.1    Tomino, I.2    Tanimoto, Y.3    Nishizawa, M.4


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