Memory of chirality trapping of low inversion barrier 1,4-benzodiazepin-2- one enolates

Tetrahedron Asymmetry

Volumn 16, Issue 18, 2005, Pages 2998-3002

  Carlier, Paul R ^a   Lam, Polo C H ^a   DeGuzman, Joseph C ^a   Zhao, Hongwu ^a  

^a VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZODIAZEPIN 2 ONE DERIVATIVE;

ALKYLATION; ARTICLE; CHIRALITY; ENANTIOMER; PRIORITY JOURNAL;

EID: 24944499725     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.08.017     Document Type: Article

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8. The only previously published route to such compounds involves lipase-catalyzed acylation of prochiral 3,3-bis(hydroxymethyl)-1,4- benzodiazepin-2-ones: A. Avdagic, A. Lesac, Z. Majer, M. Hollosi, and V. Sunjic Helv. Chim. Acta 81 1998 1567 1582
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14. R(S): 18.5 min [Chiralpak AD (0.46 cm × 25 cm, Daicel Chemical Ind., Ltd.) hexane/i-PrOH, 90/10, 1.0 mL/min] 100% ee.
15. rac) + ln(h/2kT)]: H. Eyring Chem. Rev. 17 1935 65 77
16. R(R): 16.5 min [Chiralpak AD (0.46 cm × 25 cm, Daicel Chemical Ind., Ltd.) hexane/i-PrOH, 90/10, 1.0 mL/min] 97% ee.