Organic Letters
Letter
amination/transition-metal-catalyzed cyclization reactions. Chem. -
Eur. J. 2014, 20, 3040. (g) Xu, K.; Gilles, T.; Breit, B. Asymmetric
synthesis of N-allylic indoles via regio- and enantioselective allylation
of aryl hydrazines. Nat. Commun. 2015, 6, 7616.
(6) Shenvi, R. A.; O’Malley, D. P.; Baran, P. S. Chemoselectivity: the
mother of invention in total synthesis. Acc. Chem. Res. 2009, 42, 530.
(7) Trost, B. M.; Crawley, M. L. Asymmetric transition-metal-
catalyzed allylic alkylations: applications in total synthesis. Chem. Rev.
2003, 103, 2921.
(8) Liu, G.; Wu, Y. Palladium-catalyzed allylic C-H bond
functionalization of olefins. Top. Curr. Chem. 2009, 292, 195.
(9) (a) McNeill, E.; Ritter, T. 1,4-Functionalization of 1,3-dienes
with low-valent iron catalysts. Acc. Chem. Res. 2015, 48, 2330.
(b) McCammant, M. S.; Liao, L.; Sigman, M. S. Palladium-catalyzed
1,4-difunctionalization of butadiene to form skipped polyenes. J. Am.
Chem. Soc. 2013, 135, 4167. (c) Chen, Q.-A.; Kim, D. K.; Dong, V. M.
Regioselective hydroacylation of 1,3-dienes by cobalt catalysis. J. Am.
Chem. Soc. 2014, 136, 3772. (d) Tao, Z.-L.; Adili, A.; Shen, H.-C.;
Han, Z.-Y.; Gong, L.-Z. Catalytic enantioselective assembly of
homoallylic alcohols from dienes, aryldiazonium salts, and aldehydes.
Angew. Chem., Int. Ed. 2016, 55, 4322.
(15) Kumbhar, H. S.; Gadilohar, B. L.; Shankarling, G. S. Synthesis
and spectroscopic study of highly fluorescent β-enaminone based
boron complexes. Spectrochim. Acta, Part A 2015, 146, 80.
(16) Choe, J.; Yang, J.; Park, K.; Palani, T.; Lee, S. Nickel-catalyzed
decarboxylative coupling reaction of alkynyl carboxylic acids and allyl
acetates. Tetrahedron Lett. 2012, 53, 6908.
(17) (a) Trost, B. M.; Schmidt, T. A simple synthesis of dienones via
isomerization of alkynones effected by palladium catalysts. J. Am.
Chem. Soc. 1988, 110, 2301. (b) Gao, S.; Liu, H.; Yang, C.; Fu, Z.;
Yao, H.; Lin, A. Accessing 1,3-dienes via palladium-catalyzed allylic
alkylation of pronucleophiles with skipped enynes. Org. Lett. 2017, 19,
4710. (c) Su, Y.-L.; Li, L.-L.; Zhou, X.-L.; Dai, Z.-Y.; Wang, P.-S.;
Gong, L.-Z. Asymmetric α-allylation of aldehydes with alkynes by
integrating chiral hydridopalladium and enamine catalysis. Org. Lett.
2018, 20, 2403.
(10) For selected examples, see: (a) Trost, B. M.; Bunt, R. C. On the
effect of the nature of ion pairs as nucleophiles in a metal-catalyzed
substitution reaction. J. Am. Chem. Soc. 1998, 120, 70. (b) Zheng, W.-
H.; Sun, N.; Hou, X.-L. Highly regio- and enantioselective palladium-
catalyzed allylic alkylation and amination of dienyl esters with 1,1’-
P,N-ferrocene ligands. Org. Lett. 2005, 7, 5151. (c) Trost, B. M.;
Hansmann, M. M.; Thaisrivongs, D. A. Palladium-catalyzed alkylation
of 1,4-dienes by C-H activation. Angew. Chem., Int. Ed. 2012, 51,
4950. (d) Howell, J. M.; Liu, W.; Young, A. J.; White, M. C. General
allylic C−H alkylation with tertiary nucleophiles. J. Am. Chem. Soc.
2014, 136, 5750. (e) Wang, P.-S.; Liu, P.; Zhai, Y.-J.; Lin, H.-C.; Han,
Z.-Y.; Gong, L.-Z. Asymmetric allylic C−H oxidation for the synthesis
of chromans. J. Am. Chem. Soc. 2015, 137, 12732. (f) Lin, H.-C.;
Wang, P.-S.; Tao, Z.-L.; Chen, Y.-G.; Han, Z.-Y.; Gong, L.-Z. Highly
enantioselective allylic C−H alkylation of terminal olefins with
pyrazol-5-ones enabled by cooperative catalysis of palladium complex
and Brønsted acid. J. Am. Chem. Soc. 2016, 138, 14354.
(11) (a) van Leeuwen, P. W. N. M.; Kamer, P. C. J.; Reek, J. N. H.;
Dierkes, P. Ligand bite angle effects in metal-catalyzed C−C bond
formation. Chem. Rev. 2000, 100, 2741. (b) Kamer, P. C. J.; van
Leeuwen, P. W. N. M.; Reek, J. N. H. Wide bite angle diphosphines:
Xantphos ligands in transition metal complexes and catalysis. Acc.
Chem. Res. 2001, 34, 895. (c) Niemeyer, Z. L.; Milo, A.; Hickey, D. P.;
Sigman, M. S. Parameterization of phosphine ligands reveals
mechanistic pathways and predicts reaction outcomes. Nat. Chem.
2016, 8, 610. (d) Cruz, F. A.; Chen, Z.; Kurtoic, S. I.; Dong, V. M.
Tandem Rh-catalysis: decarboxylative β-keto acid and alkyne cross-
coupling. Chem. Commun. 2016, 52, 5836. (e) Wu, K.; Doyle, A. G.
Parameterization of phosphine ligands demonstrates enhancement of
nickel catalysis via remote steric effects. Nat. Chem. 2017, 9, 779.
(12) Lin, A.; Yang, J.; Hashim, M. N-Indolyltriethylborate: a useful
reagent for synthesis of C3-quaternary indolenines. Org. Lett. 2013,
15, 1950.
(13) (a) Wu, W.-T.; Zhang, L.; You, S.-L. Catalytic asymmetric
dearomatization (CADA) reactions of phenol and aniline derivatives.
Chem. Soc. Rev. 2016, 45, 1570. (b) Tu, H.-F.; Zheng, C.; Xu, R.-Q.;
Liu, X.-J.; You, S.-L. Iridium-catalyzed intermolecular asymmetric
dearomatization of β-naphthols with allyl alcohols or allyl ethers.
Angew. Chem., Int. Ed. 2017, 56, 3237. (c) Fang, X.; Zeng, Y.; Li, Q.;
Wu, Z.; Yao, H.; Lin, A. Redox-neutral atom-economic Pd(0)-
catalyzed dearomatization of β-naphthols with alkynes toward
naphthalenones. Org. Lett. 2018, 20, 2530.
(14) Zheng, J.; Deng, L.; Chen, M.; Xiao, X.; Xiao, S.; Guo, C.; Xiao,
G.; Bai, L.; Ye, W.; Zhang, D.; Chen, H. Elaboration of thorough
simplified vinca alkaloids as antimitotic agents based on pharmaco-
phore similarity. Eur. J. Med. Chem. 2013, 65, 158.
E
Org. Lett. XXXX, XXX, XXX−XXX