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Volumn 67, Issue 21, 2002, Pages 7275-7282

Toward a computational tool predicting the stereochemical outcome of asymmetric reactions. 1. Application to sharpless asymmetric dihydroxylation

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC REACTION;

EID: 0037131196     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0258148     Document Type: Article
Times cited : (38)

References (49)
  • 4
  • 18
    • 0037074089 scopus 로고    scopus 로고
    • (b) Mnemonic device predicts the outcome of AD on similar substrates; see, for example: Dominique, R.; Roy, R. Tetrahedron Lett. 2002, 43, 395-398.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 395-398
    • Dominique, R.1    Roy, R.2
  • 23
    • 0035042831 scopus 로고    scopus 로고
    • During the course of our work, synthetic investigations on substrate binding were reported. Bayer, A.; Svendsen, J. S. Eur. J. Org. Chem. 2001, 1769-1780.
    • (2001) Eur. J. Org. Chem. , pp. 1769-1780
    • Bayer, A.1    Svendsen, J.S.2
  • 24
    • 2142786433 scopus 로고    scopus 로고
    • Private communication
    • QM/MM accuracy can be reached using carefully parametrized force fields. Nonbonded interactions, which are extremely important in differentiating paths in asymmetric synthesis, are problematic in most QM approaches but well described by empirical parameters. Norrby, P.-O. Private communication.
    • Norrby, P.-O.1
  • 25
    • 0033862856 scopus 로고    scopus 로고
    • For an excellent account of enantiodiscriminating binding, see: Lipkowitz, K. B. Acc. Chem. Res. 2000, 33, 555-562.
    • (2000) Acc. Chem. Res. , vol.33 , pp. 555-562
    • Lipkowitz, K.B.1
  • 46
    • 2142734622 scopus 로고    scopus 로고
    • note
    • 26a However, Seebach had disclosed the (2R,3R)- and (2S,3S)-α-methylthreonines but neither (2R,3S) nor (2S,3R) that were expected by Goodman's approach.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.