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Volumn 131, Issue 50, 2009, Pages 18168-18176

Complete mapping of the stereochemical course of retentive deprotonation/alkylation of 1H-benzo[e][1,4]diazepin-2(3H)-ones

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION PARAMETER; CHIRAL INTERMEDIATES; COMPLETE MAPPINGS; DENSITY-FUNCTIONAL CALCULATIONS; DIAZEPINE; ELECTROPHILES; ENANTIOPURE; ENOLATES; RING FUSION; RING INVERSION; SILYL ENOL ETHERS; STEREOLABILE; TORSIONAL EFFECT; TRANSITION STRUCTURES;

EID: 72449178946     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja907507j     Document Type: Article
Times cited : (14)

References (60)
  • 22
    • 0042929265 scopus 로고    scopus 로고
    • Denmark, S. E., Ed.; John Wiley & Sons, Inc.: New York
    • Kawabata, T.; Fuji, K. In Topics in Stereochemistry; Denmark, S. E., Ed.; John Wiley & Sons, Inc.: New York, 2003; Vol.23, pp 175-205.
    • (2003) Topics in Stereochemistry , vol.23 , pp. 175-205
    • Kawabata, T.1    Fuji, K.2
  • 28
    • 56949101540 scopus 로고    scopus 로고
    • We have previously made this distinction in ref 4. We also commend Wolf's recent description of these reactions as examples of "selfregeneration of chiral elements with stereolabile intermediates" Royal Society of Chemistry: Cambridge, UK
    • We have previously made this distinction in ref 4. We also commend Wolf's recent description of these reactions as examples of "selfregeneration of chiral elements with stereolabile intermediates" (Wolf, C. In Dynamic Stereochemistry of Chiral Compounds: Principles and Applications; Royal Society of Chemistry: Cambridge, UK, 2008; pp 282-289).
    • (2008) Dynamic Stereochemistry of Chiral Compounds: Principles and Applications , pp. 282-289
    • Wolf, C.1
  • 30
    • 72449137836 scopus 로고    scopus 로고
    • note
    • We use the helical descriptors (M)- and (P)- to assign the sense of chirality of the ring, according to the sign of the C2N1C10C11 dihedral angle (M = minus, P = positive). This dihedral angle has the same sign as the C2C3N4C5 dihedral, which has historically (see ref 22) been used to describe the conformation of the BZD ring.
  • 35
    • 72449177085 scopus 로고    scopus 로고
    • note
    • 1H NMR spectroscopy at room temperature (see refs 2-4).
  • 36
    • 72449202381 scopus 로고    scopus 로고
    • Crystallographic data (cif) are given in the Supporting Information and has been deposited as CCDC-696626 at the
    • Crystallographic data (cif) are given in the Supporting Information and has been deposited as CCDC-696626 at the Cambridge Crystallographic Data Centre (www.ccdc.cam.ac.uk/data-request/cif).
  • 37
    • 72449131123 scopus 로고    scopus 로고
    • Crystallographic data (cif) and details on the use of anomalous dispersion effects to determine absolute configuration are given in the Supporting Information. This structure has also been deposited as CCDC-696624 at the
    • Crystallographic data (cif) and details on the use of anomalous dispersion effects to determine absolute configuration are given in the Supporting Information. This structure has also been deposited as CCDC-696624 at the Cambridge Crystallographic Data Centre (www.ccdc.cam.ac.uk/data-request/ cif).
  • 39
    • 72449123423 scopus 로고    scopus 로고
    • Crystallographic data (cif) and details on the use of anomalous dispersion effects to determine absolute configuration are given in the Supporting Information. The structure has also been deposited as CCDC-696625 at the
    • Crystallographic data (cif) and details on the use of anomalous dispersion effects to determine absolute configuration are given in the Supporting Information. The structure has also been deposited as CCDC-696625 at the Cambridge Crystallographic Data Centre (www.ccdc.cam.ac.uk/data-request/cif) .
  • 40
    • 72449145054 scopus 로고    scopus 로고
    • note
    • Activation free energies of enantiomerization of 16.8 (356 K) and 16.0 (195 K) kcal/mol respectively were determined (see ref 14).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.