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Volumn 127, Issue 4, 2005, Pages 1080-1081

Brønsted acid catalysis of achiral enamine for regio- and enantioselective nitroso aldol synthesis

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; ACID; GLYCOLIC ACID; METHANOL; NITROSO ALDOL; NITROSO DERIVATIVE; TOLUENE; UNCLASSIFIED DRUG; ALDEHYDE; AMINE;

EID: 13644253047     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0444637     Document Type: Article
Times cited : (269)

References (61)
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    • (2004) Proc. Natl. Acad. Sci. U.S.A. , vol.101 , pp. 5846-5850
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    • For the enantioselective nitroso aldol reaction and related papers, see: (a) Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2003, 125, 6038-6039. 2004, 126, 6498. (b) Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 5360-5361. (c) See ref 4c. (d) Momiyama, N.; Torii, H.; Saito, S.; Yamamoto, H. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5374-5378. (e) Yamamoto, Y.; Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 5962-5963. (f) Mathew, S. P.; Iwamura, H.; Blackmond, D. G. Angew. Chem., Int. Ed. 2004, 43, 3317-3321. (g) Córdova, A.; Sundén, H.; Bøgevig, A.; Johansson, M.; Himo, F. Chem. Eur. J. 2004, 10, 3673-3684. (h) Hayashi, Y.; Yamaguchi, J.; Sumiya, T.; Hibino, K.; Shoji, M. J. Org. Chem. 2004, 69, 5966-5973. (i) Hayashi, Y.; Yamaguchi, J.; Hibino, K.; Sumiya, T.; Urushima, T.; Shoji, M.; Hashizumi, D.; Koshino, H. Adv. Synth. Catal. 2004, 346, 1435-1439. (j) Wang, W.; Wang, J.; Li, H.; Liao, L. Tetrahedron Lett. 2004, 45, 7235-7238. (k) Iwamura, H.; Wells, D. H.; Mathew, S. P.; Klussmann, M.; Armstrong, A.; Blackmond, D. G. J. Am. Chem. Soc. 2004, 126, 16312-16313.
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    • For the enantioselective nitroso aldol reaction and related papers, see: (a) Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2003, 125, 6038-6039. 2004, 126, 6498. (b) Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 5360-5361. (c) See ref 4c. (d) Momiyama, N.; Torii, H.; Saito, S.; Yamamoto, H. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5374-5378. (e) Yamamoto, Y.; Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 5962-5963. (f) Mathew, S. P.; Iwamura, H.; Blackmond, D. G. Angew. Chem., Int. Ed. 2004, 43, 3317-3321. (g) Córdova, A.; Sundén, H.; Bøgevig, A.; Johansson, M.; Himo, F. Chem. Eur. J. 2004, 10, 3673-3684. (h) Hayashi, Y.; Yamaguchi, J.; Sumiya, T.; Hibino, K.; Shoji, M. J. Org. Chem. 2004, 69, 5966-5973. (i) Hayashi, Y.; Yamaguchi, J.; Hibino, K.; Sumiya, T.; Urushima, T.; Shoji, M.; Hashizumi, D.; Koshino, H. Adv. Synth. Catal. 2004, 346, 1435-1439. (j) Wang, W.; Wang, J.; Li, H.; Liao, L. Tetrahedron Lett. 2004, 45, 7235-7238. (k) Iwamura, H.; Wells, D. H.; Mathew, S. P.; Klussmann, M.; Armstrong, A.; Blackmond, D. G. J. Am. Chem. Soc. 2004, 126, 16312-16313.
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    • For the enantioselective nitroso aldol reaction and related papers, see: (a) Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2003, 125, 6038-6039. 2004, 126, 6498. (b) Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 5360-5361. (c) See ref 4c. (d) Momiyama, N.; Torii, H.; Saito, S.; Yamamoto, H. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5374-5378. (e) Yamamoto, Y.; Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 5962-5963. (f) Mathew, S. P.; Iwamura, H.; Blackmond, D. G. Angew. Chem., Int. Ed. 2004, 43, 3317-3321. (g) Córdova, A.; Sundén, H.; Bøgevig, A.; Johansson, M.; Himo, F. Chem. Eur. J. 2004, 10, 3673-3684. (h) Hayashi, Y.; Yamaguchi, J.; Sumiya, T.; Hibino, K.; Shoji, M. J. Org. Chem. 2004, 69, 5966-5973. (i) Hayashi, Y.; Yamaguchi, J.; Hibino, K.; Sumiya, T.; Urushima, T.; Shoji, M.; Hashizumi, D.; Koshino, H. Adv. Synth. Catal. 2004, 346, 1435-1439. (j) Wang, W.; Wang, J.; Li, H.; Liao, L. Tetrahedron Lett. 2004, 45, 7235-7238. (k) Iwamura, H.; Wells, D. H.; Mathew, S. P.; Klussmann, M.; Armstrong, A.; Blackmond, D. G. J. Am. Chem. Soc. 2004, 126, 16312-16313.
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    • See ref 4c
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    • For the enantioselective nitroso aldol reaction and related papers, see: (a) Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2003, 125, 6038-6039. 2004, 126, 6498. (b) Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 5360-5361. (c) See ref 4c. (d) Momiyama, N.; Torii, H.; Saito, S.; Yamamoto, H. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5374-5378. (e) Yamamoto, Y.; Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 5962-5963. (f) Mathew, S. P.; Iwamura, H.; Blackmond, D. G. Angew. Chem., Int. Ed. 2004, 43, 3317-3321. (g) Córdova, A.; Sundén, H.; Bøgevig, A.; Johansson, M.; Himo, F. Chem. Eur. J. 2004, 10, 3673-3684. (h) Hayashi, Y.; Yamaguchi, J.; Sumiya, T.; Hibino, K.; Shoji, M. J. Org. Chem. 2004, 69, 5966-5973. (i) Hayashi, Y.; Yamaguchi, J.; Hibino, K.; Sumiya, T.; Urushima, T.; Shoji, M.; Hashizumi, D.; Koshino, H. Adv. Synth. Catal. 2004, 346, 1435-1439. (j) Wang, W.; Wang, J.; Li, H.; Liao, L. Tetrahedron Lett. 2004, 45, 7235-7238. (k) Iwamura, H.; Wells, D. H.; Mathew, S. P.; Klussmann, M.; Armstrong, A.; Blackmond, D. G. J. Am. Chem. Soc. 2004, 126, 16312-16313.
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    • For the enantioselective nitroso aldol reaction and related papers, see: (a) Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2003, 125, 6038-6039. 2004, 126, 6498. (b) Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 5360-5361. (c) See ref 4c. (d) Momiyama, N.; Torii, H.; Saito, S.; Yamamoto, H. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5374-5378. (e) Yamamoto, Y.; Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 5962-5963. (f) Mathew, S. P.; Iwamura, H.; Blackmond, D. G. Angew. Chem., Int. Ed. 2004, 43, 3317-3321. (g) Córdova, A.; Sundén, H.; Bøgevig, A.; Johansson, M.; Himo, F. Chem. Eur. J. 2004, 10, 3673-3684. (h) Hayashi, Y.; Yamaguchi, J.; Sumiya, T.; Hibino, K.; Shoji, M. J. Org. Chem. 2004, 69, 5966-5973. (i) Hayashi, Y.; Yamaguchi, J.; Hibino, K.; Sumiya, T.; Urushima, T.; Shoji, M.; Hashizumi, D.; Koshino, H. Adv. Synth. Catal. 2004, 346, 1435-1439. (j) Wang, W.; Wang, J.; Li, H.; Liao, L. Tetrahedron Lett. 2004, 45, 7235-7238. (k) Iwamura, H.; Wells, D. H.; Mathew, S. P.; Klussmann, M.; Armstrong, A.; Blackmond, D. G. J. Am. Chem. Soc. 2004, 126, 16312-16313.
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    • For the enantioselective nitroso aldol reaction and related papers, see: (a) Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2003, 125, 6038-6039. 2004, 126, 6498. (b) Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 5360-5361. (c) See ref 4c. (d) Momiyama, N.; Torii, H.; Saito, S.; Yamamoto, H. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5374-5378. (e) Yamamoto, Y.; Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 5962-5963. (f) Mathew, S. P.; Iwamura, H.; Blackmond, D. G. Angew. Chem., Int. Ed. 2004, 43, 3317-3321. (g) Córdova, A.; Sundén, H.; Bøgevig, A.; Johansson, M.; Himo, F. Chem. Eur. J. 2004, 10, 3673-3684. (h) Hayashi, Y.; Yamaguchi, J.; Sumiya, T.; Hibino, K.; Shoji, M. J. Org. Chem. 2004, 69, 5966-5973. (i) Hayashi, Y.; Yamaguchi, J.; Hibino, K.; Sumiya, T.; Urushima, T.; Shoji, M.; Hashizumi, D.; Koshino, H. Adv. Synth. Catal. 2004, 346, 1435-1439. (j) Wang, W.; Wang, J.; Li, H.; Liao, L. Tetrahedron Lett. 2004, 45, 7235-7238. (k) Iwamura, H.; Wells, D. H.; Mathew, S. P.; Klussmann, M.; Armstrong, A.; Blackmond, D. G. J. Am. Chem. Soc. 2004, 126, 16312-16313.
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    • Iwamura, H.1    Wells, D.H.2    Mathew, S.P.3    Klussmann, M.4    Armstrong, A.5    Blackmond, D.G.6
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    • See ref 7d
    • See ref 7d.
  • 43
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    • note
    • Detailed results are described in the Supporting Information.
  • 44
    • 13644255103 scopus 로고    scopus 로고
    • note
    • The results are summarized in the Supporting Information.
  • 45
    • 13644255050 scopus 로고    scopus 로고
    • note
    • Unfortunately, this system did not afford enough enantioselectivity for enamines of aldehydes and acyclic ketones.
  • 60
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    • See ref 6i
    • (f) See ref 6i.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.