DOI: 10.1016/j.tetlet.2003.10.058. One-pot selective cleavage of prenyl carbamates using iodine in methanol followed by zinc

One-pot selective cleavage of prenyl carbamates using iodine in methanol followed by zinc

10.1016/j.tetlet.2003.10.058

Crossref journal-article

Elsevier BV

Tetrahedron Letters (78)

Bibliography

VatÃ¨le, J.-M. (2003). One-pot selective cleavage of prenyl carbamates using iodine in methanol followed by zinc. Tetrahedron Letters, 44(51), 9127â9129.

Authors 1

Jean-Michel Vatèle (first)

References 15 Referenced 14

Kocienski, P. J. Protecting Groups; Thieme: Stuggart, 1994; Chapter 6
Greene, T. W.; Wuts, P. G. M. Protecting Groups in Organic Synthesis; 3rd ed., John Wiley and Sons Inc.: New York, 1999; Chapter 7. (10.1002/0471220574)
10.1055/s-2001-18765 / Synlett by Vatèle (2001)
10.1055/s-2002-20480 / Synlett by Vatèle (2002)
10.1016/S0040-4020(02)00539-2 / Tetrahedron by Vatèle (2002)
{'key': '10.1016/j.tetlet.2003.10.058_BIB8', 'series-title': 'Heterocyclic Fragmentation of Organic Molecules', 'first-page': '49', 'author': 'Ho', 'year': '1993'} / Heterocyclic Fragmentation of Organic Molecules by Ho (1993)
10.1055/s-2002-31919 / Synlett by Mineno (2002)
{'key': '10.1016/j.tetlet.2003.10.058_BIB10', 'series-title': 'Handbook of Grignard Reagents', 'first-page': '53', 'author': 'Rieke', 'year': '1996'} / Handbook of Grignard Reagents by Rieke (1996)
Activation of zinc by iodine is precedented, see for example: (a) Palmer, M. H.; Reid, J. A. J. Chem. Soc. 1960, 931–938; (10.1039/JR9600000931)
(b) Huo, S. Org. Lett. 2003, 5, 423–425. (10.1021/ol0272693)
{'key': '10.1016/j.tetlet.2003.10.058_BIB12', 'first-page': '185', 'volume': '7', 'author': 'Garst', 'year': '2000'} by Garst (2000)
10.1021/ja00490a082 / J. Am. Chem. Soc. by Young (1978)
This Zn-mediated intramolecular transesterification is reminiscent of the intramolecular cleavage of phosphodiesters catalyzed by Zn(II) coordinated to amines: (a) Mollenveld, P.; Engbersen, J. F. J.; Reinhoudt, D. N. Chem. Soc. Rev. 2000, 29, 75–86; (b) Bonfà, L.; Gatos, M.; Mancin, F.; Teulla, P.; Tonellato, U. Inorg. Chem. 2003, 42, 3943–3949. (10.1021/ic034139x)
Until now, only one method to deprotect the N-Preoc group has been described: Lemaire-Audoire, S.; Savignac, M.; Pourcelot, G.; Genêt, J.-P.; Bernard, J.-M. J. Mol. Cat. A: Chem. 1997, 116, 247–258.
10.1021/jo01045a515 / J. Org. Chem. by Rachele (1963)

Dates

Type	When
Created	21 years, 9 months ago (Nov. 24, 2003, 10:38 a.m.)
Deposited	5 years, 5 months ago (March 27, 2020, 6:04 a.m.)
Indexed	1 year, 8 months ago (Jan. 2, 2024, 6:39 a.m.)
Issued	21 years, 9 months ago (Dec. 1, 2003)
Published	21 years, 9 months ago (Dec. 1, 2003)
Published Print	21 years, 9 months ago (Dec. 1, 2003)

Funders 0

None

BibTeX

@article{Vat_le_2003, title={One-pot selective cleavage of prenyl carbamates using iodine in methanol followed by zinc}, volume={44}, ISSN={0040-4039}, url={http://dx.doi.org/10.1016/j.tetlet.2003.10.058}, DOI={10.1016/j.tetlet.2003.10.058}, number={51}, journal={Tetrahedron Letters}, publisher={Elsevier BV}, author={Vatèle, Jean-Michel}, year={2003}, month=dec, pages={9127–9129} }

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