DOI: 10.1002/jhet.5570260360. Behaviour of aminoacids and aliphatic aldehydes in dipolar aprotic solvents: Formation of oxazolidinones—behaviour of aminoacids and aliphatic aldehydes in dipolar aprotic solvents

Behaviour of aminoacids and aliphatic aldehydes in dipolar aprotic solvents: Formation of oxazolidinones—behaviour of aminoacids and aliphatic aldehydes in dipolar aprotic solvents

10.1002/jhet.5570260360

Crossref journal-article

Wiley

Journal of Heterocyclic Chemistry (311)

Abstract

AbstractReactions of aliphatic branched aldehydes with proline in dimethyl sulfoxide or acetonitrile solution afford oxazolidin‐5‐ones with high diastereoselection. Linear aldehydes afford aldolic/crotonic condensation products; with short reaction times, the presence of Oxazolidinones can be detected in the pmr spectra. Acyclic aminoacids and branched aldehydes yield a reaction mixture the pmr and ir spectra of which give evidence for iminic‐oxazolidinone equilibria. The structure of (2R,5S)‐2‐trichloromethyl‐1‐aza‐3‐oxabiciclo‐[3.3.0]octan‐4‐one has been confirmed by X‐ray diffraction analysis.

Bibliography

Orsini, F., Pelizzoni, F., Forte, M., Sisti, M., Bombieri, G., & Benetollo, F. (1989). Behaviour of aminoacids and aliphatic aldehydes in dipolar aprotic solvents: Formation of oxazolidinonesâbehaviour of aminoacids and aliphatic aldehydes in dipolar aprotic solvents. Journal of Heterocyclic Chemistry, 26(3), 837â841. Portico.

Authors 6

F. Orsini (first)
F. Pelizzoni (additional)
M. Forte (additional)
M. Sisti (additional)
G. Bombieri (additional)
F. Benetollo (additional)

References 16 Referenced 34

{'key': 'e_1_2_1_2_2', 'first-page': '569', 'volume': '115', 'author': 'Forte M.', 'year': '1985', 'journal-title': 'Gazz. Chim. Ital.'} / Gazz. Chim. Ital. by Forte M. (1985)
M.Forte F.OrsiniandF.PelizzoniJ. Heterocyclic Chem. in press.
Unpublished results byA.TreasurywalaandC.Angst Diplomtar‐beit ETH Zurich 1975.
10.1021/ja00354a034
10.1007/BF00498180
10.1002/ange.19860980330
10.1002/ardp.19863190515
10.1002/ardp.19863190618
10.1002/ange.19590711006
10.1016/S0040-4020(01)96506-8
R.Grigg J.Idle P.McMeekinandD.Vipond J. Chem. Soc. Chem. Commun. 49(1987). (10.1039/c39870000049)
J. M.GullandandT. M.Mead J. Chem. Soc. 210(1935) (10.1039/jr9350000210)
10.1016/0022-2364(74)90154-1
10.1021/ja00839a011
{'key': 'e_1_2_1_10_2', 'volume-title': 'SHELX” program for crystal structure determination', 'author': 'Sheldrick M. G.', 'year': '1976'} / SHELX” program for crystal structure determination by Sheldrick M. G. (1976)
{'key': 'e_1_2_1_11_2', 'volume-title': 'International tables for X‐Ray Crystallography', 'year': '1974'} / International tables for X‐Ray Crystallography (1974)

Dates

Type	When
Created	16 years, 5 months ago (March 11, 2009, 3:57 p.m.)
Deposited	1 year, 10 months ago (Oct. 21, 2023, 11:43 p.m.)
Indexed	1 year, 5 months ago (March 16, 2024, 3:20 a.m.)
Issued	36 years, 4 months ago (May 1, 1989)
Published	36 years, 4 months ago (May 1, 1989)
Published Online	16 years, 5 months ago (March 11, 2009)
Published Print	36 years, 4 months ago (May 1, 1989)

Funders 0

None

BibTeX

@article{Orsini_1989, title={Behaviour of aminoacids and aliphatic aldehydes in dipolar aprotic solvents: Formation of oxazolidinones—behaviour of aminoacids and aliphatic aldehydes in dipolar aprotic solvents}, volume={26}, ISSN={1943-5193}, url={http://dx.doi.org/10.1002/jhet.5570260360}, DOI={10.1002/jhet.5570260360}, number={3}, journal={Journal of Heterocyclic Chemistry}, publisher={Wiley}, author={Orsini, F. and Pelizzoni, F. and Forte, M. and Sisti, M. and Bombieri, G. and Benetollo, F.}, year={1989}, month=may, pages={837–841} }

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