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Reactivity of (R)-4-phenyloxazolidin-2-thione chiral auxiliary: from deprotection to heterocyclic interconversion

(2008) HETEROCYCLES. 75(10). p.2459-2475
Author
Organization
Abstract
Using (R)-3-beilzyl-4-phenyloxazolidin-2-thione (2) as model compound, a sequence of reactions has been established that allows the chiral auxiliary deprotection to furnish a primary amine. Treatment of 2 with ethyl triflate (3b) followed by ring opening with RbI (4b) and HI elimination with DBU, in a one pot process, gave S-ethyl-N-benzyl-N-1-phenylvinylcarbamothioate (5, 95% yield) which acid hydrolysis (9) and saponification liberated benzylamine. Through a mechanistic study, we showed that the activated chiral oxazolidin-2-thione 3b is a tunable intermediate towards the corresponding oxazolidin-2-one 7, thiazolidin-2-one 8 and thiazolidin-2-thione 10. All those reactions were chemoselective and preserved the chiral center. A structural analysis of this series of heterocycles, by NMR and X-ray diffraction, has been performed.
Keywords
Oxazolidin-2-one, Oxazolidine-2-thione, Thiazolidin-2-one, Thiazolidine-2-thione

Citation

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MLA
Monbaliu, Jean-Christophe, Bernard Tinant, and Jacqueline Marchand-Brynaert. “Reactivity of (R)-4-phenyloxazolidin-2-thione Chiral Auxiliary: From Deprotection to Heterocyclic Interconversion.” HETEROCYCLES 75.10 (2008): 2459–2475. Print.
APA
Monbaliu, J.-C., Tinant, B., & Marchand-Brynaert, J. (2008). Reactivity of (R)-4-phenyloxazolidin-2-thione chiral auxiliary: from deprotection to heterocyclic interconversion. HETEROCYCLES, 75(10), 2459–2475.
Chicago author-date
Monbaliu, Jean-Christophe, Bernard Tinant, and Jacqueline Marchand-Brynaert. 2008. “Reactivity of (R)-4-phenyloxazolidin-2-thione Chiral Auxiliary: From Deprotection to Heterocyclic Interconversion.” Heterocycles 75 (10): 2459–2475.
Chicago author-date (all authors)
Monbaliu, Jean-Christophe, Bernard Tinant, and Jacqueline Marchand-Brynaert. 2008. “Reactivity of (R)-4-phenyloxazolidin-2-thione Chiral Auxiliary: From Deprotection to Heterocyclic Interconversion.” Heterocycles 75 (10): 2459–2475.
Vancouver
1.
Monbaliu J-C, Tinant B, Marchand-Brynaert J. Reactivity of (R)-4-phenyloxazolidin-2-thione chiral auxiliary: from deprotection to heterocyclic interconversion. HETEROCYCLES. 2008;75(10):2459–75.
IEEE
[1]
J.-C. Monbaliu, B. Tinant, and J. Marchand-Brynaert, “Reactivity of (R)-4-phenyloxazolidin-2-thione chiral auxiliary: from deprotection to heterocyclic interconversion,” HETEROCYCLES, vol. 75, no. 10, pp. 2459–2475, 2008.
@article{520851,
  abstract     = {Using (R)-3-beilzyl-4-phenyloxazolidin-2-thione (2) as model compound, a sequence of reactions has been established that allows the chiral auxiliary deprotection to furnish a primary amine. Treatment of 2 with ethyl triflate (3b) followed by ring opening with RbI (4b) and HI elimination with DBU, in a one pot process, gave S-ethyl-N-benzyl-N-1-phenylvinylcarbamothioate (5, 95% yield) which acid hydrolysis (9) and saponification liberated benzylamine. Through a mechanistic study, we showed that the activated chiral oxazolidin-2-thione 3b is a tunable intermediate towards the corresponding oxazolidin-2-one 7, thiazolidin-2-one 8 and thiazolidin-2-thione 10. All those reactions were chemoselective and preserved the chiral center. A structural analysis of this series of heterocycles, by NMR and X-ray diffraction, has been performed.},
  author       = {Monbaliu, Jean-Christophe and Tinant, Bernard and Marchand-Brynaert, Jacqueline},
  issn         = {0385-5414},
  journal      = {HETEROCYCLES},
  keywords     = {Oxazolidin-2-one,Oxazolidine-2-thione,Thiazolidin-2-one,Thiazolidine-2-thione},
  language     = {eng},
  number       = {10},
  pages        = {2459--2475},
  title        = {Reactivity of (R)-4-phenyloxazolidin-2-thione chiral auxiliary: from deprotection to heterocyclic interconversion},
  volume       = {75},
  year         = {2008},
}

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