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Am. Chem. Soc."},{"key":"ref2\/cit2","unstructured":"For reviews on Cr-mediated carbon\u2212carbon bond-forming reactions, see:"},{"key":"ref2\/cit2a","doi-asserted-by":"crossref","first-page":"991","DOI":"10.1021\/cr9703360","volume":"99","author":"F\u00fcrstner A.","year":"1999","journal-title":"Chem. Rev."},{"key":"ref2\/cit2b","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1055\/s-1999-3672","author":"Wessjohann L. A.","year":"1999","journal-title":"Synthesis"},{"key":"ref2\/cit2c","doi-asserted-by":"crossref","first-page":"123","DOI":"10.2183\/pjab.76.123","volume":"76","author":"Takai K.","year":"2000","journal-title":"Proc. Japan Acad. Ser. B"},{"key":"ref2\/cit2d","unstructured":"dSaccomano, N. A.Comprehensive Organic Synthesis,Trost, B. M.; Fleming, I.Eds.Pergamon,Oxford, 1991, Vol.1, 173."},{"key":"ref3\/cit3","unstructured":"For Cr-mediated enantioselective allylation, see:"},{"key":"ref3\/cit3a","doi-asserted-by":"crossref","first-page":"73","DOI":"10.1080\/00397918308061961","volume":"13","author":"Cazes B.","year":"1983","journal-title":"Synth. Commun."},{"key":"ref3\/cit3b","doi-asserted-by":"crossref","first-page":"5386","DOI":"10.1021\/jo00122a011","volume":"60","author":"Chen C.","year":"1995","journal-title":"J. Org. Chem."},{"key":"ref3\/cit3c","doi-asserted-by":"crossref","first-page":"5031","DOI":"10.1021\/ol047661b","volume":"6","author":"Namba K.","year":"2004","journal-title":"Org. Lett."},{"key":"ref3\/cit3d","doi-asserted-by":"crossref","first-page":"2322","DOI":"10.1021\/jo970069y","volume":"62","author":"Sugimoto K.","year":"1997","journal-title":"J. Org. 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Soc."},{"key":"ref4\/cit4","unstructured":"For reviews on metal-mediated enantioselective allylation, for example, see:"},{"key":"ref4\/cit4a","doi-asserted-by":"crossref","first-page":"243","DOI":"10.1021\/ar00139a002","volume":"20","author":"Yamamoto Y.","year":"1987","journal-title":"Acc. Chem. Res."},{"key":"ref4\/cit4b","doi-asserted-by":"crossref","first-page":"31","DOI":"10.1021\/cr950037f","volume":"96","author":"Marshall J. A.","year":"1996","journal-title":"Chem. Rev."},{"key":"ref4\/cit4c","doi-asserted-by":"crossref","first-page":"2763","DOI":"10.1021\/cr020050h","volume":"103","author":"Denmark S. E.","year":"2003","journal-title":"Chem. Rev."},{"key":"ref5\/cit5a","doi-asserted-by":"crossref","first-page":"4796","DOI":"10.1021\/ja00302a042","volume":"107","author":"Uemura D.","year":"1985","journal-title":"J. Am. Chem. 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Chem."},{"key":"ref6\/cit6","unstructured":"For the synthetic work on the marine natural product halichondrins from this laboratory, see:"},{"key":"ref6\/cit6a","doi-asserted-by":"crossref","first-page":"3162","DOI":"10.1021\/ja00034a086","volume":"114","author":"Aicher T. D.","year":"1992","journal-title":"J. Am. Chem. Soc."},{"key":"ref6\/cit6b","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1351\/pac200375010001","volume":"75","author":"Choi H.-w.","year":"2003","journal-title":"Pure Appl. Chem."},{"key":"ref6\/cit6c","doi-asserted-by":"crossref","first-page":"7770","DOI":"10.1021\/ja047826b","volume":"126","author":"Namba K.","year":"2004","journal-title":"J. Am. Chem. Soc."},{"key":"ref6\/cit6d","doi-asserted-by":"crossref","first-page":"15382","DOI":"10.1021\/ja055966v","volume":"127","author":"Namba K.","year":"2005","journal-title":"J. Am. Chem. 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D.","year":"1991","journal-title":"Tetrahedron Lett."},{"key":"ref7\/cit7d","doi-asserted-by":"crossref","first-page":"9382","DOI":"10.1021\/jo051479m","volume":"70","author":"Lambert W. T.","year":"2005","journal-title":"J. Org. Chem."},{"key":"ref7\/cit7e","doi-asserted-by":"crossref","first-page":"38","DOI":"10.1055\/s-1994-22730","author":"Horita K.","year":"1994","journal-title":"Synlett"},{"key":"ref7\/cit7f","first-page":"386","author":"Horita K.","year":"2000","journal-title":"Phytochem. Phytopharm."},{"key":"ref7\/cit7g","doi-asserted-by":"crossref","first-page":"5299","DOI":"10.1021\/ol702559e","volume":"9","author":"Henderson J. A.","year":"2007","journal-title":"Org. Lett."},{"key":"ref8\/cit8a","doi-asserted-by":"crossref","first-page":"5551","DOI":"10.1016\/j.bmcl.2004.08.069","volume":"14","author":"Zheng W.","year":"2004","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref8\/cit8b","volume-title":"Anticancer Agents from Natural Products","author":"Yu M. J.","year":"2005"},{"key":"ref8\/cit8c","unstructured":"cLittlefield, B. A.; Palme, M. H.; Seletsky, B. M.; Towle, M. J.; Yu, M. J.; Zheng, W.U.S. Patents 6214865 and 6365759 and International Patent WO99\/65894."},{"key":"ref9\/cit9a","doi-asserted-by":"crossref","first-page":"5495","DOI":"10.1021\/ja00196a082","volume":"111","author":"Corey E. J.","year":"1989","journal-title":"J. Am. Chem. Soc."},{"key":"ref10\/cit10","unstructured":"This ligand was synthesized as depicted below. For the details, see theSupporting Information."},{"key":"ref11\/cit11","unstructured":"In addition to 2,6-dimethylbenzylsulfonamideB, 2-methylbenzyl- 2,4-dimethylbenzyl- and 2,5-dimethylbenzylsulfonamides were tested, but all of them existed as oils. Using the procedure shown in ref(10), we attempted to synthesize 2,4,6-trimethylbenzylsulfonyl chloride, but unsuccessfully."},{"key":"ref12\/cit12","unstructured":"The tested conditions included: complexation at rt for 45 min, 1.5 h, and 2.5 h; complexation at 42 \u00b0C for 45 min, 1.5 h, and 2.5 h. We attempted to follow the complexation event by react IR spectroscopy, but the result was not conclusive. Therefore, we relied on the overall performance (asymmetric induction and yield) of 2-haloallylation to draw this conclusion. We should note that, with this optimized complexation protocol, the reproducibility of 2-haloallylation was also improved."},{"key":"ref13\/cit13","doi-asserted-by":"crossref","first-page":"12349","DOI":"10.1021\/ja9625236","volume":"118","author":"F\u00fcrstner A.","year":"1996","journal-title":"J. Am. Chem. Soc."},{"key":"ref14\/cit14","doi-asserted-by":"crossref","first-page":"5031","DOI":"10.1021\/ol047661b","volume":"6","author":"Namba K.","year":"2004","journal-title":"Org. Lett."},{"key":"ref15\/cit15","unstructured":"The catalyst loading was tested for the case of2 + 4a \u2192 7a; the following results were obtained: 10 mol % (yield = 85%, ee = 93%), 5 mol % (yield = 76%, ee = 92%), and 2.5 mol % (yield = 60%, ee = 91%)."},{"key":"ref16\/cit16","unstructured":"The optical purity of4bused was better than 99%."},{"key":"ref18\/cit18","unstructured":"For the determination of absolute configuration, seeSupporting Informationof reference 1."},{"key":"ref19\/cit19","unstructured":"In the catalytic system, Cr(III) is reduced to Cr(II) by Mn in situ."},{"key":"ref20\/cit20","unstructured":"For this combination of substrates, the time to completion, yield, and de were 15 h, 81%, and 99%, respectively, with CrBr3, whereas they were 40 h, 73%, and 92%, respectively, with CrCl3\u00b73THF."},{"key":"ref21\/cit21","unstructured":"For a review on this subject, see:"},{"key":"ref21\/cit21a","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1002\/anie.198500013","volume":"24","author":"Masamune S.","year":"1985","journal-title":"Angew. Chem., Int. Ed. Engl."},{"key":"ref23\/cit23","unstructured":"This recovered ligand was shown to be as effective (asymmetric induction, yield, and reproducibility) as the original ligand."}],"container-title":["Organic Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/ol801093p","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,3,6]],"date-time":"2023-03-06T17:03:25Z","timestamp":1678122205000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/ol801093p"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2008,6,13]]},"references-count":61,"journal-issue":{"issue":"14","published-print":{"date-parts":[[2008,7,17]]}},"alternative-id":["10.1021\/ol801093p"],"URL":"https:\/\/doi.org\/10.1021\/ol801093p","relation":{},"ISSN":["1523-7060","1523-7052"],"issn-type":[{"value":"1523-7060","type":"print"},{"value":"1523-7052","type":"electronic"}],"subject":[],"published":{"date-parts":[[2008,6,13]]}}}