Top Buy Now Summary References
Home
>
Section
>
Chapter

1-Naphthyl-TADDOL/Emim BF4: a new catalytic system for the asymmetric addition of Chan's diene to aromatic aldehydes

Villano, R.; Acocella, M.; Sio, V.; Scettri, A.

Open Chemistry 8(6): 1172-1178

2010

ISSN/ISBN: 2391-5420
DOI: 10.2478/s11532-010-0100-5
Accession: 080856976

Full-Text Article emailed within 0-6 h
Payments are secure & encrypted
Powered by Stripe
Powered by PayPal

Summary
A new organocatalytic system was tested as a promoter for the asymmetric addition of Chan's diene to aldehydes under solvent-free conditions. This new organocatalyst generated in situ by mixing 1-naphthyl-TADDOL derivative and Emim BF4 was able to give enantioenriched vinylogous aldols and hetero-Diels-Alder cycloadducts. A mechanistic investigation through the detection of nonlinear effects confirmed the involvement of the ionic liquid in the formation of a new catalytic supramolecular species.

References

Emilio Fernández-Mateos; Beatriz Maciá; Miguel Yus 2012: Catalytic Asymmetric Addition of Alkyllithium Reagents to Aromatic Aldehydes European Journal of Organic Chemistry 2012(20)
Fernandezmateos, E.; Macia, B.; Yus, M. 2012: Catalytic Asymmetric Addition of Alkyllithium Reagents to Aromatic Aldehydes European Journal of Organic Chemistry (20): 3732-3736
Wang, X.; Zhang, J.; Liu, Y.; Cui, Y. 2014: Chiral Porous TADDOL-Embedded Organic Polymers for Asymmetric Diethylzinc Addition to Aldehydes Bulletin of the Chemical Society of Japan 87(3): 435-440
Hailes, H.C. 1999: Novel Recyclable Aminoalcohol Salts in Catalytic Asymmetric Inductions. the Addition of Diethylzinc to Aromatic Aldehydes Synlett 1999(1): 105-107
Wu, Y.; Yun, H.; Wu, Y.; Ding, K.; Zhou, Y. 2000: Synthesis of N-α-pyridylmethyl amino alcohols and application in catalytic asymmetric addition of diethylzinc to aromatic aldehydes Tetrahedron: Asymmetry 11(17): 3543-3552
Brunel, J.; Constantieux, T.; Legrand, O.; Buono, G. 1998: New chiral o-hydroxyphenyl diazaphospholidine oxide. Catalytic application in asymmetric addition of diethylzinc to aromatic aldehydes Tetrahedron Letters 39(19): 2961-2964
Rueping, M.; Volla, C.M.R.; Atodiresei, I. 2012: Catalytic asymmetric addition of aldehydes to oxocarbenium ions: a dual catalytic system for the synthesis of chromenes Organic Letters 14(17): 4642-4645
Zhang, L.; Tu, B.; Ge, M.; Li, Y.; Chen, L.; Wang, W.; Zhou, S. 2015: Asymmetric Addition of Pyridyl Aluminum Reagents to Aldehydes Catalyzed by a Titanium(IV) Catalytic System of (R)-H8-BINOLate Journal of Organic Chemistry 80(16): 8307-8313
Hayashi, T.; Tokunaga, N.; Okamoto, K.; Shintani, R. 2005: Asymmetric 1,4-Addition of Arylboronic Acids to α,β-Unsaturated Aldehydes Catalyzed by a Chiral Diene–Rhodium Complex Chemistry Letters 34(11): 1480-1481
Rosaria Villano; Maria Rosaria Acocella; Antonio Massa; Laura Palombi; Arrigo Scettri 2009: Solvent-free asymmetric vinylogous aldol reaction of Chans diene with aromatic aldehydes catalyzed by hydrogen bonding Tetrahedron 65(28): 5571-5576
Hou, C.; Peng, B.; Ye, S.; Yin, Z.; Cao, J.; Xiao, X.; Zhao, B. 2022: Catalytic asymmetric α C(sp 3)–H addition of benzylamines to aldehydes Nature Catalysis 5(11): 1061-1068
Zhang, A.; Yang, L.; Yang, N.; Liu, D. 2014: Investigation of catalytic activity and catalytic mechanism of chiral amino diol tridentate ligands in the asymmetric addition of aldehydes in the present of methyllithium reagent Journal of Organometallic Chemistry 768: 50-55
Balaji, P.V.; Li, Z.; Saito, A.; Kumagai, N.; Shibasaki, M. 2020: Direct Catalytic Asymmetric Addition of α-Fluoronitriles to Aldehydes Chemistry 26(67): 15524-15527
Veguillas, M.; Solà, R.; Shaw, L.; Maciá, B. 2016: Catalytic Asymmetric Addition of Organolithium Reagents to Aldehydes European Journal of Organic Chemistry 9: 1788-1794
Wang, Y.; Lin, J.; Wei, K. 2014: Aromatic l-prolinamide-catalyzed asymmetric Michael addition of aldehydes to nitroalkenes Tetrahedron: Asymmetry 25(24): 1599-1604
Karen M. Miller; Elizabeth A. Colby; Katrina S. Woodin; Timothy F. Jamison 2005: Asymmetric Catalytic Reductive Coupling of 1,3-Enynes and Aromatic Aldehydes Advanced Synthesis and Catalysis 347(11-13): 1533-1536
Paquin, J.-F.ço.; Stephenson, C.R.J.; Defieber, C.; Carreira, E.M. 2005: Catalytic asymmetric synthesis with rh-diene complexes: 1,4-addition of arylboronic acids to unsaturated esters Organic Letters 7(17): 3821-3824
Jiang, F.; Chen, K.-W.; Wu, P.; Zhang, Y.-C.; Jiao, Y.; Shi, F. 2019: A Strategy for Synthesizing Axially Chiral Naphthyl-Indoles: Catalytic Asymmetric Addition Reactions of Racemic Substrates Angewandte Chemie 58(42): 15104-15110
Greeves, N.; Pease, J. 1996: Enantioselective addition of tris(TADDOL) organocerium reagents to aldehydes Tetrahedron Letters 37(32): 5821-5824
Irina Iovel; Günther Oehme; Edmunds Lukevics 1998: Catalytic enantioselective addition of diethylzinc to (hetero)aromatic aldehydes Applied Organometallic Chemistry 12(7): 469-474