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Volumn 49, Issue 14, 2010, Pages 2539-2541

Enantioselective symmetry breaking directed by the order of process steps

Author keywords

Additives; Chiral resolution; Crystal growth; Dissolution; Symmetry breaking

Indexed keywords

CHIRAL RESOLUTION; CHIRAL RESOLUTIONS; CRYSTAL GROWTH AND DISSOLUTION; ENANTIOSELECTIVE; GLASS BEAD; MIXTURE COMPONENTS; PROCESS STEPS; RACEMIC MIXTURES; SYMMETRY-BREAKING; UNDERLYING MECHANISM;

EID: 77950285663     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.200907231     Document Type: Article
Times cited : (34)

References (32)
  • 19
    • 77950191190 scopus 로고    scopus 로고
    • For a recent overview of grinding-induced asymmetric transformations, see
    • For a recent overview of grinding-induced asymmetric transformations, see:
  • 28
    • 77950266200 scopus 로고    scopus 로고
    • note
    • We observed that even an ee value of 0.2% can fully overrule the additive effect and thus dictate the final outcome. However, this enantiomeric excess is too small to measure accurately by HPLC (the limit is approximately 0.5% ee).
  • 29
    • 77950241043 scopus 로고    scopus 로고
    • note
    • We confirmed that enantiomerically pure phenylglycine (2) can also direct the enantiomeric outcome of the deracemization starting from a clear solution in nucleation experiments with this compound (see the Supporting Information).
  • 30
    • 77950201667 scopus 로고    scopus 로고
    • The total crystal surface area is especially relevant in terms of the effectiveness of the additive at low concentrations, as in the current experiments.
    • The total crystal surface area is especially relevant in terms of the effectiveness of the additive at low concentrations, as in the current experiments.
  • 31
    • 77950231616 scopus 로고    scopus 로고
    • note
    • [21] Candidates from this screen are then ground under racemizing conditions. In these early studies, often the enantiomerically pure compound is not yet available to direct the symmetry breaking. However, it is often observed that the solid phase diverges spontaneously toward one handedness as a result of contamination by a chiral impurity. A simple reversal of the experimental procedure can now be used to yield the opposite handedness. In this way, elaborate and time-consuming asymmetric synthetic procedures may be avoided.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.