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Volumn 15, Issue 1, 2017, Pages 34-50

Recent advances in the chemistry of metallated azetidines

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; NITROGEN; STEREOCHEMISTRY; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

EID: 85006874545     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/C6OB01665K     Document Type: Review
Times cited : (97)

References (100)
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    • (2011) Modern Heterocyclic Chemistry , vol.1 , pp. 163-268
    • Rousseau, G.1    Robin, S.2
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    • Seebach, D.1    Lubosch, W.2
  • 59
    • 33846939147 scopus 로고    scopus 로고
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    • R. E. Gawley, S.O'Connor and R.Klein, in Science of Synthesis, ed. V. Snieckus and M. Majewski, Thieme, Stuttgart, 2006, vol. 8a, pp. 677-757
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  • 75
    • 85006956434 scopus 로고    scopus 로고
    • The NMR-determined rotational barriers for N-thiopivaloyl-2-methylazetidine and N-Boct-2-methylazetidine at 25 °C (70.7 and 75.0 kJ molrespectively) indicate rotation half-lives (for the major conformer) of 0.3 and 1.6 s. However, these extend to 2.1 and 116 days at −78 °C, strongly suggesting that rotamer interconversion is not significant under lithiation condition
    • The NMR-determined rotational barriers for N-thiopivaloyl-2-methylazetidine and N-Boct-2-methylazetidine at 25 °C (70.7 and 75.0 kJ mol−1, respectively) indicate rotation half-lives (for the major conformer) of 0.3 and 1.6 s. However, these extend to 2.1 and 116 days at −78 °C, strongly suggesting that rotamer interconversion is not significant under lithiation condition


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