Abstract
The [4+2] Diels-Alder cycloaddition has been widely used for the synthesis of six-mem-ber scaffolds. In recent years, there have been significant developments in this area, including the discovery and design of novel dienes and dienophiles with improved reactivity and selectivity. These new building blocks can be used to develop diverse molecular structures with functional group compatibility. Additionally, there is the use of catalytic systems and metal-mediated reactions to enable asymmetric [4+2] cycloadditions, resulting in enantiomerically enriched products. Over-all, recent studies related to [4+2] Diels-Alder cycloaddition using numerous dienes, dienophiles, and catalysts in different reaction conditions have significantly improved the efficiency, selectivity, and versatility of the reaction, making it an increasingly important tool in the synthesis of complex organic molecules as presented in this review. These advancements offer exciting possibilities for the development of new methods and reagents for the construction of six-membered rings and the synthesis of bioactive compounds.
[http://dx.doi.org/10.1002/9781119708841]
[http://dx.doi.org/10.1002/adsc.201100160]
[http://dx.doi.org/10.1021/cr950010w] [PMID: 11848753]
[http://dx.doi.org/10.1039/D2QO00765G]
[http://dx.doi.org/10.1002/cctc.202001195]
[http://dx.doi.org/10.1039/D0CS00365D] [PMID: 32869796]
[http://dx.doi.org/10.1002/adsc.201900028]
[http://dx.doi.org/10.1002/ejoc.201700986]
[http://dx.doi.org/10.3390/molecules26134024] [PMID: 34209381]
[http://dx.doi.org/10.1021/acs.accounts.0c00284] [PMID: 32790284]
[PMID: 21061230]
[http://dx.doi.org/10.1039/C7RA10716A]
[http://dx.doi.org/10.1002/jlac.19284600106]
[http://dx.doi.org/10.1002/anie.198007791]
[http://dx.doi.org/10.1002/ajoc.202100793]
[http://dx.doi.org/10.1002/anie.202001654] [PMID: 32662195]
[http://dx.doi.org/10.1021/cr0783986] [PMID: 18479169]
[http://dx.doi.org/10.1002/asia.201601203] [PMID: 27863108]
[http://dx.doi.org/10.1002/1521-3773(20020517)41:10<1668:AID-ANIE1668>3.0.CO;2-Z] [PMID: 19750686]
[http://dx.doi.org/10.1039/C7CS00184C] [PMID: 28660957]
[http://dx.doi.org/10.1039/C5RA17488K]
[http://dx.doi.org/10.1002/1099-0690(200102)2001:3<439:AID-EJOC439>3.0.CO;2-B]
[http://dx.doi.org/10.1021/cr078346g] [PMID: 18942879]
[http://dx.doi.org/10.1039/C5RA08306K]
[http://dx.doi.org/10.1039/C2CS35370A] [PMID: 23172010]
[http://dx.doi.org/10.3390/sym13101911]
[http://dx.doi.org/10.1002/chem.201805412] [PMID: 30664302]
[http://dx.doi.org/10.1039/C6DT03389J] [PMID: 27730228]
[http://dx.doi.org/10.3390/catal10101117]
[PMID: 17357583]
[http://dx.doi.org/10.1039/b816703f] [PMID: 19847335]
[http://dx.doi.org/10.1007/s41061-022-00398-2] [PMID: 35951264]
[http://dx.doi.org/10.3390/molecules27041304] [PMID: 35209094]
[http://dx.doi.org/10.1039/C8CS00274F] [PMID: 29993045]
[http://dx.doi.org/10.1002/cjoc.202000486]
[http://dx.doi.org/10.1039/D1CC00707F] [PMID: 33710234]
[http://dx.doi.org/10.1038/s41467-020-15599-w] [PMID: 32296076]
[http://dx.doi.org/10.1002/ejoc.202201289]
[http://dx.doi.org/10.1021/acs.joc.0c01993] [PMID: 33118353]
[http://dx.doi.org/10.1021/acs.orglett.9b00035] [PMID: 30865466]
[http://dx.doi.org/10.1021/acs.orglett.9b02629] [PMID: 31465234]
[http://dx.doi.org/10.1021/acs.joc.1c03163] [PMID: 35380043]
[http://dx.doi.org/10.1021/acs.joc.1c03072] [PMID: 35212520]
[http://dx.doi.org/10.1021/acs.joc.2c01417] [PMID: 35944162]
[http://dx.doi.org/10.1002/ajoc.202200671]
[http://dx.doi.org/10.1002/ajoc.202100401]
[http://dx.doi.org/10.1039/D2CC02458F] [PMID: 35687078]
[http://dx.doi.org/10.1039/D0QO01236J]
[http://dx.doi.org/10.1021/acs.orglett.0c03360] [PMID: 33136411]
[http://dx.doi.org/10.1002/anie.202006841] [PMID: 32662155]
[http://dx.doi.org/10.1002/anie.202000838] [PMID: 32112662]
[http://dx.doi.org/10.1002/anie.202214925] [PMID: 36347807]
[http://dx.doi.org/10.1021/acs.orglett.2c01343] [PMID: 35594569]
[http://dx.doi.org/10.1021/acs.orglett.2c01437] [PMID: 35639829]
[http://dx.doi.org/10.1039/D1QO01876K]
[http://dx.doi.org/10.1021/acs.joc.1c00558] [PMID: 33961747]
[http://dx.doi.org/10.1002/ejoc.202000822]
[http://dx.doi.org/10.1021/acs.orglett.0c02486] [PMID: 32902298]
[http://dx.doi.org/10.1021/acs.orglett.1c02539] [PMID: 34570517]
[http://dx.doi.org/10.1021/jacs.2c01656] [PMID: 35380438]
[http://dx.doi.org/10.1002/ajoc.202200382]
[http://dx.doi.org/10.1021/acs.orglett.1c04289] [PMID: 35019657]
[http://dx.doi.org/10.1016/j.carres.2022.108623] [PMID: 35738050]
[http://dx.doi.org/10.1016/j.mencom.2022.05.031]
[http://dx.doi.org/10.1016/j.molstruc.2022.134608]
[http://dx.doi.org/10.1021/acs.joc.2c00186] [PMID: 35315664]
[http://dx.doi.org/10.1002/adsc.202101401]
[http://dx.doi.org/10.1002/ejoc.202100370]
[http://dx.doi.org/10.1016/j.rechem.2021.100174]
[http://dx.doi.org/10.1039/D0CC04413J] [PMID: 32705107]
[http://dx.doi.org/10.1039/D0CC05842D] [PMID: 33179634]
[http://dx.doi.org/10.1021/acs.joc.9b01644] [PMID: 31552743]
[http://dx.doi.org/10.1002/chem.201900011] [PMID: 30697832]