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Volumn 69, Issue 12, 1996, Pages 3639-3650

Asymmetric Synthesis of Functionalized Secondary Alcohols by Catalytic Ring-Cleavage Reactions of Cyclic Acetals Derived from (R)-1,3-Butanediol

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EID: 0001312608     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.69.3639     Document Type: Article
Times cited : (27)

References (55)
  • 1
    • 0001249937 scopus 로고
    • Review: a) A. Alexakis and P. Mangency, Tetrahedron Asymmetry, 1, 477 (1990); b) D. Seebach, R. Imwinkelreid, and T. Weber, in "Modem Synthetic Methods," ed by R. Scheffold, Springer Verlag, Berlin (1986), Vol. 4, p. 125. For leading references, see also: c) K. Ishihara, N. Hanaki, and H. Yamamoto, J. Am. Chem. Soc., 115, 10695 (1993); d) S. E. Denmark and N. G. Almstead, J. Am. Chem. Soc., 113, 8089 (1991).
    • (1990) Tetrahedron Asymmetry , vol.1 , pp. 477
    • Alexakis, A.1    Mangency, P.2
  • 2
    • 0001249937 scopus 로고
    • ed by R. Scheffold, Springer Verlag, Berlin
    • Review: a) A. Alexakis and P. Mangency, Tetrahedron Asymmetry, 1, 477 (1990); b) D. Seebach, R. Imwinkelreid, and T. Weber, in "Modem Synthetic Methods," ed by R. Scheffold, Springer Verlag, Berlin (1986), Vol. 4, p. 125. For leading references, see also: c) K. Ishihara, N. Hanaki, and H. Yamamoto, J. Am. Chem. Soc., 115, 10695 (1993); d) S. E. Denmark and N. G. Almstead, J. Am. Chem. Soc., 113, 8089 (1991).
    • (1986) Modem Synthetic Methods , vol.4 , pp. 125
    • Seebach, D.1    Imwinkelreid, R.2    Weber, T.3
  • 3
    • 0043217699 scopus 로고
    • Review: a) A. Alexakis and P. Mangency, Tetrahedron Asymmetry, 1, 477 (1990); b) D. Seebach, R. Imwinkelreid, and T. Weber, in "Modem Synthetic Methods," ed by R. Scheffold, Springer Verlag, Berlin (1986), Vol. 4, p. 125. For leading references, see also: c) K. Ishihara, N. Hanaki, and H. Yamamoto, J. Am. Chem. Soc., 115, 10695 (1993); d) S. E. Denmark and N. G. Almstead, J. Am. Chem. Soc., 113, 8089 (1991).
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 10695
    • Ishihara, K.1    Hanaki, N.2    Yamamoto, H.3
  • 4
    • 0000693134 scopus 로고
    • Review: a) A. Alexakis and P. Mangency, Tetrahedron Asymmetry, 1, 477 (1990); b) D. Seebach, R. Imwinkelreid, and T. Weber, in "Modem Synthetic Methods," ed by R. Scheffold, Springer Verlag, Berlin (1986), Vol. 4, p. 125. For leading references, see also: c) K. Ishihara, N. Hanaki, and H. Yamamoto, J. Am. Chem. Soc., 115, 10695 (1993); d) S. E. Denmark and N. G. Almstead, J. Am. Chem. Soc., 113, 8089 (1991).
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 8089
    • Denmark, S.E.1    Almstead, N.G.2
  • 8
    • 0344518591 scopus 로고
    • For recent mechanistic studies, see Ref. 1d and a) S. E. Denmark and T. M. Willson. J. Am. Chem. Soc., 111, 3475 (1989); b) I. Mori, K. Ishihara, L. A. Flippin, K. Nozaki, H. Yamamoto, P. A. Bartlett, and C. H. Heathcock. J. Org. Chem., 55, 6107 (1990); c) S. E. Denmark and N. G. Almstead, J. Org. Chem., 56, 6458 (1991); d) T. Sammakia and R. S. Smith, J. Org. Chem., 57, 2997 (1992); e) T. Sammakia and R. S. Smith, J. Am. Chem. Soc., 114, 10998 (1992).
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 3475
    • Denmark, S.E.1    Willson, T.M.2
  • 9
    • 0001151568 scopus 로고
    • For recent mechanistic studies, see Ref. 1d and a) S. E. Denmark and T. M. Willson. J. Am. Chem. Soc., 111, 3475 (1989); b) I. Mori, K. Ishihara, L. A. Flippin, K. Nozaki, H. Yamamoto, P. A. Bartlett, and C. H. Heathcock. J. Org. Chem., 55, 6107 (1990); c) S. E. Denmark and N. G. Almstead, J. Org. Chem., 56, 6458 (1991); d) T. Sammakia and R. S. Smith, J. Org. Chem., 57, 2997 (1992); e) T. Sammakia and R. S. Smith, J. Am. Chem. Soc., 114, 10998 (1992).
    • (1990) J. Org. Chem. , vol.55 , pp. 6107
    • Mori, I.1    Ishihara, K.2    Flippin, L.A.3    Nozaki, K.4    Yamamoto, H.5    Bartlett, P.A.6    Heathcock, C.H.7
  • 10
    • 33751499246 scopus 로고
    • For recent mechanistic studies, see Ref. 1d and a) S. E. Denmark and T. M. Willson. J. Am. Chem. Soc., 111, 3475 (1989); b) I. Mori, K. Ishihara, L. A. Flippin, K. Nozaki, H. Yamamoto, P. A. Bartlett, and C. H. Heathcock. J. Org. Chem., 55, 6107 (1990); c) S. E. Denmark and N. G. Almstead, J. Org. Chem., 56, 6458 (1991); d) T. Sammakia and R. S. Smith, J. Org. Chem., 57, 2997 (1992); e) T. Sammakia and R. S. Smith, J. Am. Chem. Soc., 114, 10998 (1992).
    • (1991) J. Org. Chem. , vol.56 , pp. 6458
    • Denmark, S.E.1    Almstead, N.G.2
  • 11
    • 0001058317 scopus 로고
    • For recent mechanistic studies, see Ref. 1d and a) S. E. Denmark and T. M. Willson. J. Am. Chem. Soc., 111, 3475 (1989); b) I. Mori, K. Ishihara, L. A. Flippin, K. Nozaki, H. Yamamoto, P. A. Bartlett, and C. H. Heathcock. J. Org. Chem., 55, 6107 (1990); c) S. E. Denmark and N. G. Almstead, J. Org. Chem., 56, 6458 (1991); d) T. Sammakia and R. S. Smith, J. Org. Chem., 57, 2997 (1992); e) T. Sammakia and R. S. Smith, J. Am. Chem. Soc., 114, 10998 (1992).
    • (1992) J. Org. Chem. , vol.57 , pp. 2997
    • Sammakia, T.1    Smith, R.S.2
  • 12
    • 84985664814 scopus 로고
    • For recent mechanistic studies, see Ref. 1d and a) S. E. Denmark and T. M. Willson. J. Am. Chem. Soc., 111, 3475 (1989); b) I. Mori, K. Ishihara, L. A. Flippin, K. Nozaki, H. Yamamoto, P. A. Bartlett, and C. H. Heathcock. J. Org. Chem., 55, 6107 (1990); c) S. E. Denmark and N. G. Almstead, J. Org. Chem., 56, 6458 (1991); d) T. Sammakia and R. S. Smith, J. Org. Chem., 57, 2997 (1992); e) T. Sammakia and R. S. Smith, J. Am. Chem. Soc., 114, 10998 (1992).
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 10998
    • Sammakia, T.1    Smith, R.S.2
  • 20
    • 85033185570 scopus 로고    scopus 로고
    • Ref. 1c
    • A reductive cleavage of chiral cyclic acetals catalyzed by an aluminium catalyst has been reported: K. Ishihara, N. Hanaki, and H. Yamamoto, Synlett, 1993, 127, and Ref. 1c.
    • Synlett , vol.1993 , pp. 127
    • Ishihara, K.1    Hanaki, N.2    Yamamoto, H.3
  • 21
    • 0002022995 scopus 로고    scopus 로고
    • For Lewis acid-catalyzed cleavage acyclic acetals, see: a) T. Tsunoda, M. Suzuki, and R. Noyori, Tetrahedron Lett., 21, 71 (1980); b) H. Sakurai, K. Sasaki, and A. Hosomi, Tetrahedron Lett., 22, 745 (1981); c) T. Mukaiyama, H. Nagaoka, M. Murakami, and M. Ohshima, Chem. Lett., 1985, 977.
    • (1980) Tetrahedron Lett. , vol.21 , pp. 71
    • Tsunoda, T.1    Suzuki, M.2    Noyori, R.3
  • 22
    • 0000816394 scopus 로고
    • For Lewis acid-catalyzed cleavage acyclic acetals, see: a) T. Tsunoda, M. Suzuki, and R. Noyori, Tetrahedron Lett., 21, 71 (1980); b) H. Sakurai, K. Sasaki, and A. Hosomi, Tetrahedron Lett., 22, 745 (1981); c) T. Mukaiyama, H. Nagaoka, M. Murakami, and M. Ohshima, Chem. Lett., 1985, 977.
    • (1981) Tetrahedron Lett. , vol.22 , pp. 745
    • Sakurai, H.1    Sasaki, K.2    Hosomi, A.3
  • 23
    • 0002022995 scopus 로고    scopus 로고
    • For Lewis acid-catalyzed cleavage acyclic acetals, see: a) T. Tsunoda, M. Suzuki, and R. Noyori, Tetrahedron Lett., 21, 71 (1980); b) H. Sakurai, K. Sasaki, and A. Hosomi, Tetrahedron Lett., 22, 745 (1981); c) T. Mukaiyama, H. Nagaoka, M. Murakami, and M. Ohshima, Chem. Lett., 1985, 977.
    • Chem. Lett. , vol.1985 , pp. 977
    • Mukaiyama, T.1    Nagaoka, H.2    Murakami, M.3    Ohshima, M.4
  • 32
    • 0028308010 scopus 로고
    • For mechanistic studies on the silyl group migration, see: a) E. M. Carreira and R. A. Singer, Tetrahedron Lett., 35, 4323 (1994); b) S. E. Denmark and C.-T. Chen, Tetrahedron Lett., 35, 4327 (1994); c) T. K. Hollis and B. Bosnich, J. Am. Chem. Soc., 117, 4570 (1995).
    • (1994) Tetrahedron Lett. , vol.35 , pp. 4323
    • Carreira, E.M.1    Singer, R.A.2
  • 33
    • 0028241174 scopus 로고
    • For mechanistic studies on the silyl group migration, see: a) E. M. Carreira and R. A. Singer, Tetrahedron Lett., 35, 4323 (1994); b) S. E. Denmark and C.-T. Chen, Tetrahedron Lett., 35, 4327 (1994); c) T. K. Hollis and B. Bosnich, J. Am. Chem. Soc., 117, 4570 (1995).
    • (1994) Tetrahedron Lett. , vol.35 , pp. 4327
    • Denmark, S.E.1    Chen, C.-T.2
  • 34
    • 1542520958 scopus 로고
    • For mechanistic studies on the silyl group migration, see: a) E. M. Carreira and R. A. Singer, Tetrahedron Lett., 35, 4323 (1994); b) S. E. Denmark and C.-T. Chen, Tetrahedron Lett., 35, 4327 (1994); c) T. K. Hollis and B. Bosnich, J. Am. Chem. Soc., 117, 4570 (1995).
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 4570
    • Hollis, T.K.1    Bosnich, B.2
  • 38
    • 85033171273 scopus 로고    scopus 로고
    • note
    • 4NF by flash chromatography afforded 8a (anti : syn=98 : 2) in 86% yield.
  • 39
    • 85033180874 scopus 로고    scopus 로고
    • note
    • 11c)
  • 41
    • 85033173614 scopus 로고    scopus 로고
    • 12
    • 12)


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