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Highly enantioselective hetero- Diels-Alder reaction of trans-1-methoxy- 2-methyl-3-trimethylsiloxybuta-1,3-diene with aromatic and aliphatic aldehydes catalyzed by 3-substituted BINOL-titanium complex.
Org Lett. 2008 Mar 20; 10(6):1299-302.OL

Abstract

3-diphenylhydroxymethyl-substituted BINOL-titanium complex prepared in situ was found to be a highly efficient catalyst for hetero-Diels-Alder reaction of diene 1 with both aromatic and aliphatic aldehydes to give 2,5-disubstituted dihydropyrone in up to 99% yield and 99% ee.

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Authors+Show Affiliations

Yang XB
Department of Chemistry, Key Laboratory of Green Chemistry and Technology (Ministry of Education), and West China Hospital, West China Medical School, Sichuan University, Chengdu, Sichuan 610041, PR China.
Feng J
No affiliation info available
Zhang J
No affiliation info available
Wang N
No affiliation info available
Wang L
No affiliation info available
Liu JL
No affiliation info available
Yu XQ
No affiliation info available

MeSH

AldehydesButadienesCatalysisMolecular StructureNaphtholsStereoisomerismTitanium

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

18303907

Citation

Yang, Xin-Bin, et al. "Highly Enantioselective Hetero- Diels-Alder Reaction of Trans-1-methoxy- 2-methyl-3-trimethylsiloxybuta-1,3-diene With Aromatic and Aliphatic Aldehydes Catalyzed By 3-substituted BINOL-titanium Complex." Organic Letters, vol. 10, no. 6, 2008, pp. 1299-302.
Yang XB, Feng J, Zhang J, et al. Highly enantioselective hetero- Diels-Alder reaction of trans-1-methoxy- 2-methyl-3-trimethylsiloxybuta-1,3-diene with aromatic and aliphatic aldehydes catalyzed by 3-substituted BINOL-titanium complex. Org Lett. 2008;10(6):1299-302.
Yang, X. B., Feng, J., Zhang, J., Wang, N., Wang, L., Liu, J. L., & Yu, X. Q. (2008). Highly enantioselective hetero- Diels-Alder reaction of trans-1-methoxy- 2-methyl-3-trimethylsiloxybuta-1,3-diene with aromatic and aliphatic aldehydes catalyzed by 3-substituted BINOL-titanium complex. Organic Letters, 10(6), 1299-302. https://doi.org/10.1021/ol8001706
Yang XB, et al. Highly Enantioselective Hetero- Diels-Alder Reaction of Trans-1-methoxy- 2-methyl-3-trimethylsiloxybuta-1,3-diene With Aromatic and Aliphatic Aldehydes Catalyzed By 3-substituted BINOL-titanium Complex. Org Lett. 2008 Mar 20;10(6):1299-302. PubMed PMID: 18303907.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Highly enantioselective hetero- Diels-Alder reaction of trans-1-methoxy- 2-methyl-3-trimethylsiloxybuta-1,3-diene with aromatic and aliphatic aldehydes catalyzed by 3-substituted BINOL-titanium complex. AU - Yang,Xin-Bin, AU - Feng,Jie, AU - Zhang,Ji, AU - Wang,Na, AU - Wang,Li, AU - Liu,Jun-Liang, AU - Yu,Xiao-Qi, Y1 - 2008/02/28/ PY - 2008/2/29/pubmed PY - 2008/6/20/medline PY - 2008/2/29/entrez SP - 1299 EP - 302 JF - Organic letters JO - Org Lett VL - 10 IS - 6 N2 - 3-diphenylhydroxymethyl-substituted BINOL-titanium complex prepared in situ was found to be a highly efficient catalyst for hetero-Diels-Alder reaction of diene 1 with both aromatic and aliphatic aldehydes to give 2,5-disubstituted dihydropyrone in up to 99% yield and 99% ee. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/18303907/Highly_enantioselective_hetero__Diels_Alder_reaction_of_trans_1_methoxy__2_methyl_3_trimethylsiloxybuta_13_diene_with_aromatic_and_aliphatic_aldehydes_catalyzed_by_3_substituted_BINOL_titanium_complex_ L2 - https://doi.org/10.1021/ol8001706 DB - PRIME DP - Unbound Medicine ER -