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[4 + 3] Cycloaddition of aromatic α,β-unsaturated aldehydes and ketones with epoxides: one-step approach to synthesize seven-membered oxacycles catalyzed by Lewis acid.
J Org Chem. 2011 Jan 21; 76(2):669-72.JO

Abstract

A novel intermolecular [4 + 3] cycloaddition method to construct 1,4-dioxide seven-membered oxacycles was developed. This one-step method was carried out in the presence of catalytic amount of (C(2)H(5))(2)OBF(3) under mild conditions. Seven-membered oxacycles and some natural compounds could be easily synthesized via this protocol. Control experiments were carried out and possible mechanism for the reaction was proposed. Asymmetric reactions were proceeded and 3e was obtained with moderate ee value.

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Authors+Show Affiliations

Zhou YQ
Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing, China, 100190.
Wang NX
No affiliation info available
Zhou SB
No affiliation info available
Huang Z
No affiliation info available
Cao L
No affiliation info available

MeSH

AldehydesCatalysisCyclizationHeterocyclic OxidesKetonesLewis AcidsMolecular StructureStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

21192645

Citation

Zhou, Yu-Qiang, et al. "[4 + 3] Cycloaddition of Aromatic Α,β-unsaturated Aldehydes and Ketones With Epoxides: One-step Approach to Synthesize Seven-membered Oxacycles Catalyzed By Lewis Acid." The Journal of Organic Chemistry, vol. 76, no. 2, 2011, pp. 669-72.
Zhou YQ, Wang NX, Zhou SB, et al. [4 + 3] Cycloaddition of aromatic α,β-unsaturated aldehydes and ketones with epoxides: one-step approach to synthesize seven-membered oxacycles catalyzed by Lewis acid. J Org Chem. 2011;76(2):669-72.
Zhou, Y. Q., Wang, N. X., Zhou, S. B., Huang, Z., & Cao, L. (2011). [4 + 3] Cycloaddition of aromatic α,β-unsaturated aldehydes and ketones with epoxides: one-step approach to synthesize seven-membered oxacycles catalyzed by Lewis acid. The Journal of Organic Chemistry, 76(2), 669-72. https://doi.org/10.1021/jo101669t
Zhou YQ, et al. [4 + 3] Cycloaddition of Aromatic Α,β-unsaturated Aldehydes and Ketones With Epoxides: One-step Approach to Synthesize Seven-membered Oxacycles Catalyzed By Lewis Acid. J Org Chem. 2011 Jan 21;76(2):669-72. PubMed PMID: 21192645.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - [4 + 3] Cycloaddition of aromatic α,β-unsaturated aldehydes and ketones with epoxides: one-step approach to synthesize seven-membered oxacycles catalyzed by Lewis acid. AU - Zhou,Yu-Qiang, AU - Wang,Nai-Xing, AU - Zhou,Shu-Bao, AU - Huang,Zhong, AU - Cao,Linghua, Y1 - 2010/12/30/ PY - 2011/1/4/entrez PY - 2011/1/5/pubmed PY - 2011/5/20/medline SP - 669 EP - 72 JF - The Journal of organic chemistry JO - J Org Chem VL - 76 IS - 2 N2 - A novel intermolecular [4 + 3] cycloaddition method to construct 1,4-dioxide seven-membered oxacycles was developed. This one-step method was carried out in the presence of catalytic amount of (C(2)H(5))(2)OBF(3) under mild conditions. Seven-membered oxacycles and some natural compounds could be easily synthesized via this protocol. Control experiments were carried out and possible mechanism for the reaction was proposed. Asymmetric reactions were proceeded and 3e was obtained with moderate ee value. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/21192645/[4_+_3]_Cycloaddition_of_aromatic_αβ_unsaturated_aldehydes_and_ketones_with_epoxides:_one_step_approach_to_synthesize_seven_membered_oxacycles_catalyzed_by_Lewis_acid_ L2 - https://doi.org/10.1021/jo101669t DB - PRIME DP - Unbound Medicine ER -