Citation: Zhang Zi-Jing, Tao Zhong-Lin, Arafate Adele, Gong Liu-Zhu. Asymmetric Carbonyl Allylation of Aldehydes with Allylic Alcohols under the Sequential Catalysis of Palladium Complex and Chiral Phosphoric Acid[J]. Acta Chimica Sinica, ;2017, 75(12): 1196-1201. doi: 10.6023/A17080372 shu

Asymmetric Carbonyl Allylation of Aldehydes with Allylic Alcohols under the Sequential Catalysis of Palladium Complex and Chiral Phosphoric Acid

a.
School of Chemistry and Materials Science, University of Science and Technology of China, Hefei 230026
b.
Hefei National Laboratory for Physical Sciences at Microscale, Hefei 230036

Corresponding author: Gong Liu-Zhu, gonglz@ustc.edu.cn
Received Date: 14 August 2017
Available Online: 9 December 2017
Fund Project: the National Natural Science Foundation of China 21232007Project supported by the National Natural Science Foundation of China (No. 21232007)

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The asymmetric carbonyl allylation of aldehydes with allylmetal reagents presents one of the most efficient and straightforward methods for the synthesis of optically active homoallylic alcohols, which have found widespread applications in organic synthesis. As such, a wide range of chiral catalysts, including Lewis acids, Lewis bases and Br nsted acids have been reported to enable highly stereoselective carbonyl allylation of aldehydes with allylmetal reagents. Among them, chiral phosphoric acid-catalyzed carbonyl allylation of aldehydes with pinacol allylboronates represents a promising method, whereas an additional operations required for the preparation of allylboronates from allyl halides or highly active allylmetallics impose some constraints on the carbonyl allylation process. In this context, the asymmetric addition of allylboronates, in situ generated from palladium-catalyzed allylborylation, to aldehydes has been reported, while stoichiometric amounts of chiral diboronate reagents are basically required. Allylic alcohols are readily available feedstock. The direct use of allylic alcohols as starting materials in asymmetric allylborylation of carbonyls is highly valuable. Herein, we will report an asymmetric carbonyl allylation of aldehydes with allylic alcohols in the presence of octamethyl-2, 2'-bi(1, 3, 2-dioxaborolane) under the sequential catalysis of a palladium complex and chiral phosphoric acid. The presence of 2.5 mol% (η³-C₃H₅)₂Pd₂Cl₂, 5 mol% P(OPh)₃ and 10 mol% chiral phosphoric acid B*H-1 enabled 4-nitrobenzaldehyde 2a to smoothly undergo the asymmetric carbonyl allylation reaction with 2-buten-1-ol 1a and octamethyl-2, 2'-bi(1, 3, 2-dioxaborolane), giving rise to the desired homoallylic alcohol product 3aa in a 99% yield and with >20:1 dr and 92% ee. Under the optimal conditions, the generality for allylic alcohol substrates was investigated to reveal that the installation of either of saturated alkyl substituents, carbon-carbon double bond or heteroatom group in the allylic alcohols allowed the target products (3ca~3fa, 3ha~3ja) to be obtained in high yields and with excellent stereoselectivities. A (Z)-allylic alcohol and branched allylic alcohols were also able to generate the target products (3ba, 3ga), successfully. Although cinnamic alcohols participated in a clean reaction, relatively lower yields and stereoselectivity were delivered (3ka and 3la). The examination of aldehydes suggested that the introduction of either electronically deficient or rich substituents to the benzene ring of benzaldehydes was tolerant and led to corresponding homoallylic alcohols in excellent yields and stereoselectivities (3ab~3ak and 3m), with the exception of o-anisaldehyde (3al). In addition, 2-naphthaldehyde, aliphatic aldehydes and enals are all good substrates and provide high yields and enantiomeric excesses as exemplified by 3-phenylpropanal and 4-methoxycinnamaldehyde (3an~3ap).
- asymmetric catalysis,
- palladium catalysis,
- chiral phosphoric acid,
- carbonyl allylation,
- allylic alcohol
1. [1]
  (a) Chemler, S. R.; Roush, W. R. In Modern Carbonyl Chemistry, Ed.: Otera, J., Wiley-VCH, Weinheim, Germany, 2000, pp. 403~490; (b) Elford, T. G.; Hall, D. G. Synthesis 2010, 893;(c) Yus, M.; González-Gómez, J. C.; Foubelo, F. Chem. Rev. 2013, 113, 5595.
2. [2]
  (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207;(b) Denmark, S. E.; Fu, J. Chem. Rev. 2003, 103, 2763;(c) Yus, M.; González-Gómez, J. C.; Foubelo, F. Chem. Rev. 2011, 111, 7774.
3. [3]
  For examples with chiral Lewis acids as catalysts, see:(a) Furuta, K.; Mouri, M.; Yamamoto, H. Synlett 1991, 561;(b) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001;(c) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467;(d) Ishiyama, T.; Ahiko, T.-A.; Miyaura, N. J. Am. Chem. Soc. 2002, 124, 12414;(e) Wada, R.; Oisaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 8910.
4. [4]
5. [5]
  For examples with chiral Br nsted acids as catalysts, see:(a) Rauniyar, V.; Hall, D. G. Angew. Chem., Int. Ed. 2006, 45, 2426;(b) Rauniyar, V.; Zhai, H.; Hall, D. G. J. Am. Chem. Soc. 2008, 130, 8481;(c) Rauniyar, V.; Hall, D. G. J. Org. Chem. 2009, 74, 4236;(d) Jain, P.; Antilla, J. C. J. Am. Chem. Soc. 2010, 132, 11884;(e) Xing, C.-H.; Liao, Y.-X.; Zhang, Y.; Sabarova, D.; Bassous, M.; Hu, Q.-S. Eur. J. Org. Chem. 2012, 1115.
6. [6]
  For other examples of asymmetric carbonyl allylation reactions, see:(a) Kim, I. S.; Ngai, M.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 14891;(b) Lou, S.; Moquist, P. N.; Schaus, S. E. J. Am. Chem. Soc. 2006, 128, 12660;(c) Barnett, D. S.; Moquist, P. N.; Schaus, S. E. Angew. Chem., Int. Ed. 2009, 48, 8679.
7. [7]
  For the selected achiral examples, see:(a) Sebelius, S.; Wallner, O. A.; Szabó, K. J. Org. Lett. 2003, 5, 3065;(b) Selander, N.; Sebelius, S.; Estay, C.; Szabó, K. J. Eur. J. Org. Chem. 2006, 4085;(c) Se-lander, N.; Kipke, A.; Sebelius, S.; Szabó, K. J. J. Am. Chem. Soc. 2007, 129, 13723;(d) Olsson, V. J.; Szabó, K. J. Angew. Chem., Int. Ed. 2007, 46, 6891;(e) Selander, N.; Szabó, K. J. Chem. Commun. 2008, 3420;(f) Zhou, Y.-H.; Wang, H.; Liu, Y.; Zhao, Y.-L.; Zhang, C.-X.; Qu, J.-P. Org. Chem. Front. 2017, 4, 1580.
8. [8]
  For the examples of using chiral diboronates, see:(a) Sebelius, S.; Szabó, K. J. Eur. J. Org. Chem. 2005, 2539;(b) Vogt, M.; Ceylan, S.; Kirschning, A. Tetrahedron 2010, 66, 6450.
9. [9]
10. [10]
  (a) Zhu, S.-F.; Qiao, X.-C.; Zhang, Y.-Z.; Wang, L.-X.; Zhou, Q.-L. Chem. Sci. 2011, 2, 1135;(b) Tsukamoto, H.; Kawase, A.; Doi, T. Chem. Commun. 2015, 51, 8027.
11. [11]
  Yatagai, M.; Yamagishi, T.; Hida, M. Bull. Chem. Soc. Jpn. 1984, 57, 823.(b) McIntosh, J. M.; Leavitt, R. K. Tetrahedron Lett. 1986, 27, 3839.(c) Jiang, Y. Z.; Liu, G.; Zhou, C. Y.; Piao, H. R.; Wu, L. J.; Mi, A. Q. Synth. Commun. 1991, 21, 1087.
12. [12]
13. [13]
  (a) Grayson, M. N.; Pellegrinet, S. C.; Goodman, J. M. J. Am. Chem. Soc. 2012, 134, 2716.(b) Wang, H.; Jain, P.; Antilla, J. C.; Houk, K. N. J. Org. Chem. 2013, 78, 1208.(c) Incerti-Pradillos, C. A.; Kabeshov, M. A.; Malkov, A. V. Angew. Chem., Int. Ed. 2013, 52, 5338.
14. [14]
15. [15]
  Jiang, G.-X.; List, B. Angew. Chem., Int. Ed. 2011, 50, 9471. doi: 10.1002/anie.v50.40
16. [16]
  Tao, Z.-L.; Zhang, W.-Q.; Chen, D.-F.; Arafate Adele; Gong, L.-Z. J. Am. Chem. Soc. 2013, 135, 9255. doi: 10.1021/ja402740q
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