title: Oxetane synthesis through the Paternò-Büchi reaction.
abstract: The Paternò-Büchi reaction is a photochemical reaction between a carbonyl compound and an alkene to give the corresponding oxetane. In this review the mechanism of the reaction is discussed. On this basis the described use in the reaction with electron rich alkenes (enolethers, enol esters, enol silyl ethers, enanines, heterocyclic compounds has been reported. The stereochemical behavior of the reaction is particularly stressed. We pointed out the reported applications of this reaction to the synthesis of naturally occuring compounds.
authors.affiliation: Dipatimento di Scienze, Università della Basilicata, Viale dell'Ateneo Lucano 19, 85100 Potenza, Italy. maurizio.dauria@unibas.it
authors.forename: Maurizio
authors.initials: M
authors.lastname: D'Auria
authors.forename: Rocco
authors.initials: R
authors.lastname: Racioppi
mesh_terms: D001547:Benzaldehydes / Q000737:chemistry; D061565:Cycloaddition Reaction; D004988:Ethers, Cyclic / Q000138:chemical synthesis*; D005609:Free Radicals / Q000737:chemistry; D005663:Furans / Q000737:chemistry; D006801:Humans; D008956:Models, Chemical; D055668:Photochemical Processes; D011789:Quantum Theory; D013237:Stereoisomerism
chemical_list: D001547:Benzaldehydes; D004988:Ethers, Cyclic; D005609:Free Radicals; D005663:Furans; C005287:oxetane; C032175:benzaldehyde
references.citation: J Org Chem. 2003 Aug 22;68(17):6611-8
references.pmid: 12919024
references.citation: Chem Commun (Camb). 2008 Nov 30;(44):5833-5
references.pmid: 19009097
references.citation: J Am Chem Soc. 2009 Dec 2;131(47):17076-7
references.pmid: 19891435
references.citation: J Am Chem Soc. 2005 Sep 21;127(37):12774-5
references.pmid: 16159251
references.citation: Org Lett. 2000 Nov 2;2(22):3457-9
references.pmid: 11082008
references.citation: J Org Chem. 2010 Aug 20;75(16):5461-9
references.pmid: 20704423
references.citation: Photochem Photobiol Sci. 2006 Jan;5(1):51-5
references.pmid: 16395427
references.citation: J Am Chem Soc. 2002 Apr 10;124(14):3600-7
references.pmid: 11929249
references.citation: Photochem Photobiol. 1967 Jul;6(7):497-500
references.pmid: 6046275
references.citation: Chemistry. 2001 Oct 15;7(20):4512-21
references.pmid: 11695686
references.citation: Photochem Photobiol Sci. 2011 Sep;10(9):1469-73
references.pmid: 21541429
references.citation: J Am Chem Soc. 2002 Mar 20;124(11):2400-1
references.pmid: 11890764
references.citation: J Org Chem. 1997 Feb 7;62(3):564-567
references.pmid: 11671450
references.citation: Pharmacol Ther. 1991 Oct;52(1):1-34
references.pmid: 1687170
references.citation: Angew Chem Int Ed Engl. 1998 Dec 31;37(24):3400-3402
references.pmid: 29711279
references.citation: Org Lett. 2000 Nov 16;2(23):3623-5
references.pmid: 11073660
references.citation: J Phys Chem B. 2007 Jul 19;111(28):8277-82
references.pmid: 17590040
references.citation: J Org Chem. 2005 Apr 1;70(7):2522-7
references.pmid: 15787538
references.citation: Org Lett. 2005 Sep 1;7(18):3969-71
references.pmid: 16119944
references.citation: Photochem Photobiol Sci. 2010 Aug;9(8):1134-8
references.pmid: 20563353
references.citation: Beilstein J Org Chem. 2011 Feb 28;7:265-9
references.pmid: 21448243
references.citation: Org Lett. 2000 Aug 24;2(17):2711-2
references.pmid: 10990434
references.citation: Org Biomol Chem. 2004 Apr 21;2(8):1113-5
references.pmid: 15064785
references.citation: J Org Chem. 1996 Dec 13;61(25):8885-8896
references.pmid: 11667869
references.citation: Beilstein J Org Chem. 2011 Jan 26;7:113-8
references.pmid: 21448247
references.citation: Photochem Photobiol Sci. 2008 Jan;7(1):98-103
references.pmid: 18167602
references.citation: Angew Chem Int Ed Engl. 2001 Dec 17;40(24):4684-4687
references.pmid: 12404384
references.citation: Chemistry. 2000 Oct 16;6(20):3838-48
references.pmid: 11073254
references.citation: Angew Chem Int Ed Engl. 1998 May 4;37(8):1110-1112
references.pmid: 29711022
references.citation: Beilstein J Org Chem. 2011 Jan 26;7:127-34
references.pmid: 21448241
references.citation: J Am Chem Soc. 2011 Mar 2;133(8):2592-604
references.pmid: 21306157
references.citation: J Am Chem Soc. 2004 Mar 10;126(9):2838-46
references.pmid: 14995201
references.citation: Chemistry. 2005 Dec 23;12(2):553-61
references.pmid: 16173098
references.citation: J Am Chem Soc. 2001 Jun 27;123(25):6191-2
references.pmid: 11414859
references.citation: J Org Chem. 2003 Dec 26;68(26):9899-906
references.pmid: 14682681
references.citation: Photochem Photobiol Sci. 2008 Nov;7(11):1332-6
references.pmid: 18958319
references.citation: Science. 1985 Feb 22;227(4689):857-63
references.pmid: 4038558
references.citation: Chem Pharm Bull (Tokyo). 1986 Aug;34(8):3102-10
references.pmid: 3098442
references.citation: J Org Chem. 2010 May 7;75(9):2989-3001
references.pmid: 20353178
references.citation: Ultrason Sonochem. 1997 Apr;4(2):109-15
references.pmid: 11237024
references.citation: Photochem Photobiol Sci. 2004 Oct;3(10):927-32
references.pmid: 15480483
references.citation: Chem Res Toxicol. 2004 Jul;17(7):857-62
references.pmid: 15257609
references.citation: Acc Chem Res. 2004 Dec;37(12):919-28
references.pmid: 15609983
references.citation: Photochem Photobiol Sci. 2003 Sep;2(9):904-13
references.pmid: 14560807
references.citation: J Org Chem. 2008 Jun 20;73(12):4539-47
references.pmid: 18494523
references.citation: J Am Chem Soc. 2001 Sep 26;123(38):9279-82
references.pmid: 11562209
references.citation: J Am Chem Soc. 2002 Mar 13;124(10):2118-9
references.pmid: 11878957
references.citation: Org Lett. 2001 Oct 18;3(21):3361-4
references.pmid: 11594834