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Volumn 20, Issue 15, 2009, Pages 1736-1741

Crystal structures of (2-substituted-5-N-tosyl)bicyclo[3.3.0]-5-azacyclooct-2-enone: a pseudo achiral crystal from enantiopure compound and a counter-example of Wallach's rule

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO[3.3.0]OCTANE DERIVATIVE; CYCLOOCTANE DERIVATIVE;

EID: 69949099324     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2009.07.013     Document Type: Article
Times cited : (9)

References (39)
  • 2
    • 0000708637 scopus 로고
    • Buergi H.B., and Dunitz J.D. (Eds), VCH, Weinheim
    • Gavezzotti A. In: Buergi H.B., and Dunitz J.D. (Eds). Structure Correlation Vol. 2 (1994), VCH, Weinheim 509-542
    • (1994) Structure Correlation , vol.2 , pp. 509-542
    • Gavezzotti, A.1
  • 11
    • 79955037244 scopus 로고    scopus 로고
    • and leading references cited therein
    • Gavezzotti A. CrystEngComm 4 (2002) 343-347 and leading references cited therein
    • (2002) CrystEngComm , vol.4 , pp. 343-347
    • Gavezzotti, A.1
  • 15
    • 0040618431 scopus 로고
    • There are studies dealing with crystallization through the pseudoinversion center irrespective of the chirality
    • There are studies dealing with crystallization through the pseudoinversion center irrespective of the chirality. Desiraju G.R., Calabrese J.C., and Harlow R.L. Acta Crystallogr., Sect. B 47 (1991) 77-86
    • (1991) Acta Crystallogr., Sect. B , vol.47 , pp. 77-86
    • Desiraju, G.R.1    Calabrese, J.C.2    Harlow, R.L.3
  • 24
    • 69949087639 scopus 로고    scopus 로고
    • note
    • For example, (R(C*),R(N))-1a is calculated to be more stable than (R(C*),S(N))-1a. However, the NMR spectra and HPLC analysis of (R)-1a with a chiral column showed peaks corresponding to only one compound. Therefore, (R)-1a can be considered as a single chiral molecule as well as a pair of diastereomers. By analogy, (RS)-1a can be considered as a pair of enantiomers or a racemate of two chiral molecules as well as all of the four stereoisomers. We also use the additional notation d#-(R or S)-1a for each of the four stereoisomers as shown in the bracket, where d# means a specific diastereomer, and (R or S) indicates the configuration around C*. Note that d1-(R)-1a and d2-(R)-1a are the mirror images of d3-(S)-1a and d4-(S)-1a, respectively. Similar notations can be applied for compound 1b.
  • 29
    • 33744720318 scopus 로고    scopus 로고
    • A previously reported counter-example of Wallach's rule
    • A previously reported counter-example of Wallach's rule. Patrick B.O., and Brock C.P. Acta Crystallogr., Sect. B 62 (2006) 488-497
    • (2006) Acta Crystallogr., Sect. B , vol.62 , pp. 488-497
    • Patrick, B.O.1    Brock, C.P.2
  • 33
    • 26144457724 scopus 로고
    • 1 (a minimum condition for possible pseudo achiral crystals for the monoclinic crystal system) were identified from CSD data since 1989. Since scrutinizing all the results would have been too time-consuming, the search results were further narrowed down with the constraint that the target molecule contained only C, H, N, O, and S atoms. The search provided 173 hits. If two molecules in an asymmetric unit were related to each other via pseudo-inversion or pseudo-mirror planes, they would have the possibility of forming a pseudo achiral crystal. However, we were not able to identify many compounds in this class so far.
    • 1 (a minimum condition for possible pseudo achiral crystals for the monoclinic crystal system) were identified from CSD data since 1989. Since scrutinizing all the results would have been too time-consuming, the search results were further narrowed down with the constraint that the target molecule contained only C, H, N, O, and S atoms. The search provided 173 hits. If two molecules in an asymmetric unit were related to each other via pseudo-inversion or pseudo-mirror planes, they would have the possibility of forming a pseudo achiral crystal. However, we were not able to identify many compounds in this class so far. Although we have some candidates for further elucidation, either the coordinates of the crystal structures or the data required for the comparison, such as the crystal structures of the racemic compounds, are lacking. Nevertheless, more cases would be expected to be found when previous and prospective crystal structures are scrutinized based on our suggestion. Valente E.J., Trager W.F., and Lingafelter E.C. Acta Crystallogr., Sect. B 32 (1976) 277-279
    • (1976) Acta Crystallogr., Sect. B , vol.32 , pp. 277-279
    • Valente, E.J.1    Trager, W.F.2    Lingafelter, E.C.3
  • 37
    • 69949093747 scopus 로고    scopus 로고
    • note
    • saint+ ver. 6.04. sax Area-Detector Integration Program. Bruker AXS. Madison, WI, 1997-2001.
  • 38
    • 69949088426 scopus 로고    scopus 로고
    • note
    • Sheldrick, G. M. sadabs Version 2.03, A Program for Empirical Absorption Correction; Universität Göttingen, 1997-2001.
  • 39
    • 69949096853 scopus 로고    scopus 로고
    • note
    • Bruker axs shelxtl version 6.10. Structure Determination Package; Bruker AXS: Madison, WI, 2000.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.