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Soc."},{"key":"ref19\/cit19z","doi-asserted-by":"crossref","first-page":"228","DOI":"10.1039\/b310963a","author":"Clayden J.","year":"2004","journal-title":"Chem. Commun."},{"key":"ref20\/cit20","unstructured":"This evolution could be less stereoselective for compounds with groups other than methyl joined to the benzylic carbon, because the conformational preferences around the C\u2212C bond would alter the relative easiness of the electrophilic approach."},{"key":"ref21\/cit21","unstructured":"Bepimers are the major or exclusive isomers obtained in reactions with other electrophiles such as carbonyls or imines, because these reactions take place on the species [Li]-2. See also ref10e."},{"key":"ref22\/cit22","unstructured":"The addition of LiCl to the reaction media induces a decrease of the stereoselectivity, but the scarce solubility of the salt precludes this effect."},{"key":"ref23\/cit23","unstructured":"Reactions with solid Ph3SnCl require more THF to be dissolved before the addition to the reaction media (whereas Bu3SnCl is liquid)."},{"key":"ref24\/cit24","unstructured":"The influence of the reactivity on the selectivity was indicated by studying the reaction with Me3SnCl under conditions of entry 4. A 66:33 mixture of diastereoisomers was instantaneously produced, suggesting that the attack of Li-2to this electrophile is faster than the establishment of the equilibrium depicted in Scheme2."},{"key":"ref25\/cit25a","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/0022-328X(83)80237-X","volume":"251","author":"Davies A. G.","year":"1983","journal-title":"J. Organomet. Chem."},{"key":"ref25\/cit25b","volume-title":"Organotin Chemistry","author":"Davies G. A.","year":"1997"},{"key":"ref26\/cit26a","doi-asserted-by":"crossref","first-page":"4048","DOI":"10.1021\/ja00745a040","volume":"93","author":"Jensen F. R.","year":"1971","journal-title":"J. Am. Chem. Soc."},{"key":"ref26\/cit26b","doi-asserted-by":"crossref","first-page":"1672","DOI":"10.1021\/ja00447a079","volume":"99","author":"Rahm A.","year":"1977","journal-title":"J. Am. Chem. Soc."},{"key":"ref26\/cit26c","doi-asserted-by":"crossref","first-page":"4397","DOI":"10.1021\/ja00509a070","volume":"101","author":"McGahey L. F.","year":"1979","journal-title":"J. Am. Chem. Soc."},{"key":"ref26\/cit26d","doi-asserted-by":"crossref","first-page":"305","DOI":"10.1016\/0022-328X(85)80046-2","volume":"286","author":"Rahm A.","year":"1985","journal-title":"J. Organomet. Chem."},{"key":"ref26\/cit26e","doi-asserted-by":"crossref","first-page":"283","DOI":"10.1016\/0022-328X(89)85139-3","volume":"376","author":"Chopa A. B.","year":"1989","journal-title":"J. Organomet. Chem."},{"key":"ref27\/cit27","doi-asserted-by":"crossref","first-page":"909","DOI":"10.1021\/om50001a024","volume":"2","author":"Kuivila H. G.","year":"1983","journal-title":"Organometallics"},{"key":"ref28\/cit28","doi-asserted-by":"crossref","first-page":"449","DOI":"10.1021\/jo01317a032","volume":"44","author":"Leibner J. E.","year":"1979","journal-title":"J. Org. Chem."},{"key":"ref29\/cit29","doi-asserted-by":"crossref","first-page":"2496","DOI":"10.1021\/ja01162a040","volume":"72","author":"Buckles R. E.","year":"1950","journal-title":"J. Am. Chem. Soc."},{"key":"ref30\/cit30","unstructured":"CCDC 701382 [(R)-10] and 701383 [(R)-11] contains the supplementary crystallographic data. These data can be obtained free of charge atwww.ccdc.cam.ac.uk\/conts\/retrieving.html[or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K. Fax: (internat.) +44(1223)336-033.deposit@ccdc.cam.ac.uk"},{"key":"ref31\/cit31","unstructured":"This oversimplification, considering that the reaction rates of the SE2 (closed) and SE2 (assisted) processes are similar, could not be true for compounds bearing groups different from Me joined to the benzylic position, because the significance of the steric effects in the transitions states resulting in the evolution fromCandDare clearly different."}],"container-title":["The Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jo802725r","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,3,9]],"date-time":"2023-03-09T07:57:22Z","timestamp":1678348642000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/jo802725r"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2009,2,11]]},"references-count":106,"journal-issue":{"issue":"5","published-print":{"date-parts":[[2009,3,6]]}},"alternative-id":["10.1021\/jo802725r"],"URL":"https:\/\/doi.org\/10.1021\/jo802725r","relation":{},"ISSN":["0022-3263","1520-6904"],"issn-type":[{"value":"0022-3263","type":"print"},{"value":"1520-6904","type":"electronic"}],"subject":[],"published":{"date-parts":[[2009,2,11]]}}}