Organic Letters
Letter
H.-J., Eds.; Wiley-VCH: Weinheim, Germany, 2010; Chapter 13, pp
219−229. (b) Loh, C. C. J.; Schmid, M.; Webster, R.; Yen, A.; Yazdi,
S. K.; Franke, P. T.; Lautens, M. Angew. Chem., Int. Ed. 2016, 55,
10074−10078.
(19) For a review on the Thorpe−Ingold effect and an example of
rate enhancement in the lactonization of hydroxyesters: (a) Jung, M.
E.; Piizzi, G. Chem. Rev. 2005, 105, 1735−1766. (b) Brenna, E.;
Distante, F.; Gatti, F. G.; Gatti, G. Catal. Sci. Technol. 2017, 7, 1497−
1507.
(20) Kurosawa, W.; Kan, T.; Fukuyama, T. Org. Synth. 2003, 186−
186.
(3) Lautens, M.; Fagnou, K. J. Am. Chem. Soc. 2001, 123, 7170−
7171.
(4) Lautens, M.; Fagnou, K.; Yang, D. J. Am. Chem. Soc. 2003, 125,
(21) An attempted kinetic resolution of racemic 2a leads to a
experimental details and associated HPLC chromatograms.
14884−14892.
(5) (a) Loh, C. C. J.; Fang, X.; Peters, B.; Lautens, M. Chem. - Eur. J.
2015, 21, 13883−13887. (b) Loh, C. C. J.; Schmid, M.; Peters, B.;
Fang, X.; Lautens, M. Angew. Chem., Int. Ed. 2016, 55, 4600−4604.
(6) (a) Fukuyama, T.; Jow, C. K.; Cheung, M. Tetrahedron Lett.
1995, 36, 6373−6374. (b) Lin, X.; Dorr, H.; Nuss, J. M. Tetrahedron
Lett. 2000, 41, 3309−3313. (c) Kan, T.; Fukuyama, T. Chem.
Commun. 2004, 353−359.
(7) (a) Sardina, F. J.; Rapoport, H. Chem. Rev. 1996, 96, 1825−
1872. (b) Singh, P.; Samanta, K.; Das, S. K.; Panda, G. Org. Biomol.
Chem. 2014, 12, 6297−6339.
(8) For examples from transition-metal catalysis: (a) Trost, B. M.;
Ariza, X. J. Am. Chem. Soc. 1999, 121, 10727−10737. (b) Liu, X.;
Hartwig, J. F. Org. Lett. 2003, 5, 1915−1918. (c) de Castro, P. P.;
Carpanez, A. G.; Amarante, G. W. Chem. - Eur. J. 2016, 22, 10294−
10318. (d) Kuang, J.; Parveen, S.; Breit, B. Angew. Chem., Int. Ed.
2017, 56, 8422−8425. (e) Bai, X.-D.; Zhang, Q.-F.; He, Y. Chem.
Commun. 2019, 55, 5547−5550.
(9) For selected recent examples: (a) Huo, X.; He, R.; Fu, J.; Zhang,
J.; Yang, G.; Zhang, W. J. Am. Chem. Soc. 2017, 139, 9819−9822.
(b) Wei, L.; Xu, S. M.; Zhu, Q.; Che, C.; Wang, C. J. Angew. Chem.,
Int. Ed. 2017, 56, 12312−12316. (c) Huo, X.; Zhang, J.; Fu, J.; He, R.;
Zhang, W. J. Am. Chem. Soc. 2018, 140, 2080−2084. (d) Wei, L.; Zhu,
Q.; Xu, S. M.; Chang, X.; Wang, C. J. J. Am. Chem. Soc. 2018, 140,
1508−1513.
(10) For selected reviews on peptidomimetic chemistry: (a) Vagner,
J.; Qu, H.; Hruby, V. J. Curr. Opin. Chem. Biol. 2008, 12, 292−296.
̈
(b) Grauer, A.; Konig, B. Eur. J. Org. Chem. 2009, 2009, 5099−5111.
(c) Avan, I.; Hall, C. D.; Katritzky, A. R. Chem. Soc. Rev. 2014, 43,
3575−3594.
(11) Cho, Y.-H.; Tseng, N.-W.; Senboku, H.; Lautens, M. Synthesis
2008, 2008, 2467−2475.
(12) The 3D X-ray crystal structure representations of 4b and ent-4g
were prepared from the corresponding crystallographic data using
́
CYLview, see: Legault, C. Y. CYLview, version 1.0b; Universite de
(13) For a review on domino reactions and relevant examples from
ARO chemistry: (a) Boyer, A.; Lautens, M. Angew. Chem., Int. Ed.
2011, 50, 7346−7349. (b) Tsui, G. C.; Ninnemann, N. M.; Hosotani,
A.; Lautens, M. Org. Lett. 2013, 15, 1064−1067. (c) Pellissier, H.
Chem. Rev. 2013, 113, 442−524.
(14) For examples of synthetic routes employed in industry:
(a) Anderson, P. S.; Baldwin, J. J.; McClure, D. E.; Lundell, G. F.;
Jones, J. H. J. Org. Chem. 1982, 47, 2184−2187. (b) Jones, J. H.
(Merck & Co., Inc.). Hexahydronaphth[1,2-b]-1,4-Oxazines. U.S.
Patent 4,420,480, 1983. (c) Jones, J. H.; Anderson, P. S.; Baldwin, J.
J.; Clineschmidt, B. V.; McClure, D. E.; Lundell, G. F.; Randall, W. C.;
Martin, G. E.; Williams, M.; Hirshfield, J. M.; Smith, G.; Lumma, P. K.
J. Med. Chem. 1984, 27, 1607−1613. (d) Minaskanian, G.; Peck, J. V.
(Whitby Research, Inc.). Substituted Naphthoxazines Useful as
Dopaminergics. Patent WO 91/19719, 1991.
(15) Wijtmans, R.; Vink, M. K.; Schoemaker, H. E.; van Delft, F. L.;
Blaauw, R. H.; Rutjes, F. P. Synthesis 2004, 2004, 641−662.
(16) (a) Krautwald, S.; Carreira, E. M. J. Am. Chem. Soc. 2017, 139,
́
5627−5639. (b) Beletskaya, I. P.; Najera, C.; Yus, M. Chem. Rev.
2018, 118, 5080−5200.
(17) Johnson, F. Chem. Rev. 1968, 68, 375−413.
(18) The reverse reaction in the presence of methanol was
additive effects in asymmetric catalysis: Hong, L.; Sun, W.; Yang, D.;
Li, G.; Wang, R. Chem. Rev. 2016, 116, 4006−4123.
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