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Synthesis 2015; 47(15): 2265-2269
DOI: 10.1055/s-0034-1378835
DOI: 10.1055/s-0034-1378835
special topic
Conjugate Addition of Diboron Catalyzed by O-Monoacyltartaric Acids
Further Information
Publication History
Received: 15 March 2015
Accepted after revision: 12 May 2015
Publication Date:
19 June 2015 (online)
Abstract
O-3,5-Di(adamantan-1-yl)benzoyltartaric acid catalyzes the conjugate addition of bis(neopentyl glycolato)diboron to α,β-unsaturated ketones with good enantioselectivity. The addition of magnesium sulfate as a dehydrating agent and benzoic acid as a co-catalyst was found to be effective.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1378835.
- Supporting Information
-
References
- 1a Carroll A.-M, O’Sullivan TP, Guiry PJ. Adv. Synth. Catal. 2005; 347: 609
- 1b Pelz NF, Woodward AR, Burks HE, Sieber JD, Morken JP. J. Am. Chem. Soc. 2004; 126: 16328
- 1c Bonet A, Sole C, Gulyás H, Fernández E. Org. Biomol. Chem. 2012; 10: 6621
- 1d Lee Y, Hoveyda AH. J. Am. Chem. Soc. 2009; 131: 3160
- 1e Ito H, Ito S, Sasaki Y, Matsuura K, Sawamura M. J. Am. Chem. Soc. 2007; 129: 14856
- 1f Beenen M, An C, Ellman JA. J. Am. Chem. Soc. 2008; 130: 6910
- 1g Solé C, Gulyás H, Fernández E. Chem. Commun. 2012; 48: 3769
- 1h Zhang S.-S, Zhao Y.-S, Tian P, Lin G.-Q. Synlett 2013; 24: 437
- 1i Hong K, Morken JP. J. Am. Chem. Soc. 2013; 135: 9252
- 2a Chinnusamy T, Feeney K, Watson CG, Leonori D, Aggarwal VK In Comprehensive Organic Synthesis . 2nd ed., Vol. 7; Knochel P, Molander GA. Elsevier; Oxford: 2014: 692-718
- 2b Brown HC, Snyder C, Rao BC. S, Zweifel G. Tetrahedron 1986; 42: 5505
- 2c Kabalka GW, Shoup TM, Goudgaon NM. Tetrahedron Lett. 1989; 30: 1483
- 3a Sandrock DL, Jean-Gérard L, Chen C.-y, Dreher SD, Molander GA. J. Am. Chem. Soc. 2010; 132: 17108
- 3b Molander GA, Wisniewski SR, Hosseini-Sarvari M. Adv. Synth. Cat. 2013; 355: 3037
- 3c Zhang C, Yun J. Org. Lett. 2013; 15: 3416
- 4a Lee J.-E, Yun J. Angew. Chem. Int. Ed. 2008; 47: 145
- 4b Lillo V, Prieto A, Bonet A, Díaz-Requejo MM, Ramírez J, Pérez PJ, Fernández E. Organometallics 2009; 28: 659
- 4c O’Brien JM, Lee K.-s, Hoveyda AH. J. Am. Chem. Soc. 2010; 132: 10630
- 4d Chen I.-H, Yin L, Itano W, Kanai M, Shibasaki M. J. Am. Chem. Soc. 2009; 131: 11664
- 4e Chen I.-H, Kanai M, Shibasaki M. Org. Lett. 2010; 12: 4098
- 4f Mantilli L, Mazet C. ChemCatChem 2010; 2: 501
- 4g Kobayashi S, Xu P, Endo T, Ueno M, Kitanosono T. Angew. Chem. Int. Ed. 2012; 51: 12763
- 4h Zhao L, Ma Y, Duan W, He F, Chen J, Song C. Org. Lett. 2012; 14: 5780
- 4i See also: Ito H, Yamanaka H, Tateiwa J, Hosomi A. Tetrahedron Lett. 2000; 41: 6821
- 5a Shiomi T, Adachi T, Toribatake K, Zhou L, Nishiyama H. Chem. Commun. 2009; 5987
- 5b Toribatake K, Zhou L, Tsuruta A, Nishiyama H. Tetrahedron 2013; 69: 3551
- 5c See also: Kabalka GW, Das NC, Das S. Tetrahedron Lett. 2002; 43: 2323
- 6a Lillo V, Geier MJ, Westcott SA, Fernández E. Org. Biomol. Chem. 2009; 7: 4674
- 6b See also: Hirano K, Yorimitsu H, Oshima K. Org. Lett. 2007; 9: 5031
- 7a Wu H, Radomkit S, O’Brien JM, Hoveyda AH. J. Am. Chem. Soc. 2012; 134: 8277
- 7b Radomkit S, Hoveyda AH. Angew. Chem. Int. Ed. 2014; 53: 3387
- 7c See also: Lee K.-s, Zhugralin AR, Hoveyda AH. J. Am. Chem. Soc. 2009; 131: 7253
- 8a Bonet A, Gulyas H, Fernández E. Angew. Chem. Int. Ed. 2010; 49: 5130
- 8b See also: Pubill-Ulldemolins C, Bonet A, Bo C, Gulyas H, Fernández E. Chem. Eur. J. 2012; 18: 1121
- 8c See also: Pubill-Ulldemolins C, Bonet A, Bo C, Gulyas H, Fernández E. Org. Biomol. Chem. 2012; 10: 9677
- 9 Ibrahem I, Breistein P, Córdova A. Chem. Eur. J. 2012; 18: 5175
- 10a Sugiura M, Tokudomi M, Nakajima M. Chem. Commun. 2010; 46: 7799
- 10b Grimblat N, Sugiura M, Pellegrinet S. J. Org. Chem. 2014; 79: 6754
- 10c Sugiura M, Kinoshita R, Nakajima M. Org. Lett. 2014; 16: 5172
- 11a Wu TR, Chong JM. J. Am. Chem. Soc. 2007; 129: 4908
- 11b Wu TR, Chong JM. J. Am. Chem. Soc. 2005; 127: 3244
- 11c Turner HM, Patel J, Niljianskul N, Chong JM. Org. Lett. 2011; 13: 5796
- 11d Lou S, Moquist PN, Schaus SE. J. Am. Chem. Soc. 2007; 129: 15398
- 11e Bishop JA, Lou S, Schaus SE. Angew. Chem. Int. Ed. 2009; 48: 4337
- 11f Barnett DS, Moquist PN, Schaus SE. Angew. Chem. Int. Ed. 2009; 48: 8672
- 11g Moquist PN, Kodama T, Schaus SE. Angew. Chem. Int. Ed. 2010; 49: 7096
- 11h Kodama T, Moquist PN, Schaus SE. Org. Lett. 2011; 13: 6316
- 11i Luan Y, Barbato KS, Moquist PN, Kodama T, Schaus SE. J. Am. Chem. Soc. 2015; 137: 3233
- 11j Lundy BJ, Jansone-Popova S, May JA. Org. Lett. 2011; 13: 4958
- 11k Le PQ, Nguyen TS, May JA. Org. Lett. 2012; 14: 6104
- 11l Nguyen TS, Yang MS, May JA. Tetrahedron Lett. 2015; 56: 3337
- 11m See also ref. 10.
- 12 Recently, May et al. revealed a similar reactivity of enones in the BINOL-catalyzed conjugate addition of styrylboronates by systematic kinetic study, see ref. 11l.
- 13 See the Supporting Information.
- 14 In the previous study (ref. 10b), smooth complexation between catalyst 1a and styrylboronic acid was observed.
- 15 Participation of MgSO4 in the enantio-determining step is unlikely, because the identical selectivity was observed even without MgSO4 (Table 1, entries 1 and 4).
- 16 Cheon CH, Yamamoto H. Org. Lett. 2010; 12: 2476
In addition to the conjugate addition, there are several enantioselective reactions for the construction of chiral carbon centers attached to boryl groups: borane or diboron additions to alkenes, allylic substitution, and diboron addition to imines. For a review on hydroboration, see:
For a leading reference on diboration of alkenes, see:
For a leading reference on proto-boration, see:
For a leading reference on allylic substitution, see:
For leading references on diboron addition to imines, see:
For leading references on enantioselective copper catalysis, see:
For enantioselective rhodium catalysis, see:
For enantioselective nickel and palladium catalysis, see:
For related catalytic mechanisms, see: