Development of new asymmetric reactions utilizing tartaric acid esters as chiral auxiliaries. The design of an efficient chiral multinucleating system

Synlett

Volumn , Issue 8, 2003, Pages 1075-1087

  Ukaji, Yutaka ^a   Inomata, Katsuhiko ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

1,3 dipolar cycloadditions; Asymmetric synthesis; Nucleophilic additions to imine derivatives; Simmons Smith reaction; Tartaric acid esters

Indexed keywords

ALLYL ALCOHOL; CYCLOPROPANE DERIVATIVE; ESTER; IMINE; ISOQUINOLINE DERIVATIVE; LASUBINE II; METAL OXIDE; NITRILE; NITRONE; OXIDE; OXIME; PLANT EXTRACT; QUINOLIZINE DERIVATIVE; TARTARIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; PROTON NUCLEAR MAGNETIC RESONANCE; SIMMONS SMITH REACTION; SYNTHESIS;

EID: 0038729635     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-39879     Document Type: Article

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78. Other examples of Mannich-type reactions: (a) Yamada, K.-I.; Moll, G.; Shibasaki, M. Synlett 2001, 980. (b) Ferraris, D.; Young, B.; Cox, C.; Dudding, T.; Drury, W. J. III; Ryzhkov, L.; Taggi, A. E.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 67. (c) Kobayashi, S.; Hamada, T.; Manabe, K. J. Am. Chem. Soc. 2002, 124, 5640. (d) Murahashi, S.-I.; Imada, Y.; Kawakami, T.; Harada, K.; Yonemushi, Y.; Tomita, N. J. Am. Chem. Soc. 2002, 124, 2888. (e) Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964; and references cited therein. (f) Strecker reaction and related reactions: Takamura, M.; Hamashima, Y.; Usuda, H.; Kanai, M.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 2000, 39, 1650. (g) See also: Funabashi, K.; Ratni, H.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 10784. (h) See also: Josephsohn, N. S.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 11594. (i) See also: Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10012; and references cited therein.
79. Other examples of Mannich-type reactions: (a) Yamada, K.-I.; Moll, G.; Shibasaki, M. Synlett 2001, 980. (b) Ferraris, D.; Young, B.; Cox, C.; Dudding, T.; Drury, W. J. III; Ryzhkov, L.; Taggi, A. E.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 67. (c) Kobayashi, S.; Hamada, T.; Manabe, K. J. Am. Chem. Soc. 2002, 124, 5640. (d) Murahashi, S.-I.; Imada, Y.; Kawakami, T.; Harada, K.; Yonemushi, Y.; Tomita, N. J. Am. Chem. Soc. 2002, 124, 2888. (e) Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964; and references cited therein. (f) Strecker reaction and related reactions: Takamura, M.; Hamashima, Y.; Usuda, H.; Kanai, M.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 2000, 39, 1650. (g) See also: Funabashi, K.; Ratni, H.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 10784. (h) See also: Josephsohn, N. S.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 11594. (i) See also: Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10012; and references cited therein.
80. Other examples of Mannich-type reactions: (a) Yamada, K.-I.; Moll, G.; Shibasaki, M. Synlett 2001, 980. (b) Ferraris, D.; Young, B.; Cox, C.; Dudding, T.; Drury, W. J. III; Ryzhkov, L.; Taggi, A. E.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 67. (c) Kobayashi, S.; Hamada, T.; Manabe, K. J. Am. Chem. Soc. 2002, 124, 5640. (d) Murahashi, S.-I.; Imada, Y.; Kawakami, T.; Harada, K.; Yonemushi, Y.; Tomita, N. J. Am. Chem. Soc. 2002, 124, 2888. (e) Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964; and references cited therein. (f) Strecker reaction and related reactions: Takamura, M.; Hamashima, Y.; Usuda, H.; Kanai, M.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 2000, 39, 1650. (g) See also: Funabashi, K.; Ratni, H.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 10784. (h) See also: Josephsohn, N. S.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 11594. (i) See also: Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10012; and references cited therein.
81. Other examples of Mannich-type reactions: (a) Yamada, K.-I.; Moll, G.; Shibasaki, M. Synlett 2001, 980. (b) Ferraris, D.; Young, B.; Cox, C.; Dudding, T.; Drury, W. J. III; Ryzhkov, L.; Taggi, A. E.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 67. (c) Kobayashi, S.; Hamada, T.; Manabe, K. J. Am. Chem. Soc. 2002, 124, 5640. (d) Murahashi, S.-I.; Imada, Y.; Kawakami, T.; Harada, K.; Yonemushi, Y.; Tomita, N. J. Am. Chem. Soc. 2002, 124, 2888. (e) Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964; and references cited therein. (f) Strecker reaction and related reactions: Takamura, M.; Hamashima, Y.; Usuda, H.; Kanai, M.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 2000, 39, 1650. (g) See also: Funabashi, K.; Ratni, H.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 10784. (h) See also: Josephsohn, N. S.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 11594. (i) See also: Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10012; and references cited therein.
82. Other examples of Mannich-type reactions: (a) Yamada, K.-I.; Moll, G.; Shibasaki, M. Synlett 2001, 980. (b) Ferraris, D.; Young, B.; Cox, C.; Dudding, T.; Drury, W. J. III; Ryzhkov, L.; Taggi, A. E.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 67. (c) Kobayashi, S.; Hamada, T.; Manabe, K. J. Am. Chem. Soc. 2002, 124, 5640. (d) Murahashi, S.-I.; Imada, Y.; Kawakami, T.; Harada, K.; Yonemushi, Y.; Tomita, N. J. Am. Chem. Soc. 2002, 124, 2888. (e) Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964; and references cited therein. (f) Strecker reaction and related reactions: Takamura, M.; Hamashima, Y.; Usuda, H.; Kanai, M.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 2000, 39, 1650. (g) See also: Funabashi, K.; Ratni, H.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 10784. (h) See also: Josephsohn, N. S.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 11594. (i) See also: Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10012; and references cited therein.
83. Other examples of Mannich-type reactions: (a) Yamada, K.-I.; Moll, G.; Shibasaki, M. Synlett 2001, 980. (b) Ferraris, D.; Young, B.; Cox, C.; Dudding, T.; Drury, W. J. III; Ryzhkov, L.; Taggi, A. E.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 67. (c) Kobayashi, S.; Hamada, T.; Manabe, K. J. Am. Chem. Soc. 2002, 124, 5640. (d) Murahashi, S.-I.; Imada, Y.; Kawakami, T.; Harada, K.; Yonemushi, Y.; Tomita, N. J. Am. Chem. Soc. 2002, 124, 2888. (e) Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964; and references cited therein. (f) Strecker reaction and related reactions: Takamura, M.; Hamashima, Y.; Usuda, H.; Kanai, M.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 2000, 39, 1650. (g) See also: Funabashi, K.; Ratni, H.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 10784. (h) See also: Josephsohn, N. S.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 11594. (i) See also: Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10012; and references cited therein.
84. Other examples of Mannich-type reactions: (a) Yamada, K.-I.; Moll, G.; Shibasaki, M. Synlett 2001, 980. (b) Ferraris, D.; Young, B.; Cox, C.; Dudding, T.; Drury, W. J. III; Ryzhkov, L.; Taggi, A. E.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 67. (c) Kobayashi, S.; Hamada, T.; Manabe, K. J. Am. Chem. Soc. 2002, 124, 5640. (d) Murahashi, S.-I.; Imada, Y.; Kawakami, T.; Harada, K.; Yonemushi, Y.; Tomita, N. J. Am. Chem. Soc. 2002, 124, 2888. (e) Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964; and references cited therein. (f) Strecker reaction and related reactions: Takamura, M.; Hamashima, Y.; Usuda, H.; Kanai, M.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 2000, 39, 1650. (g) See also: Funabashi, K.; Ratni, H.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 10784. (h) See also: Josephsohn, N. S.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 11594. (i) See also: Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10012; and references cited therein.
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