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Organocatalytic Enantioselective Vinylogous Aldol Reaction of Allyl Aryl Ketones to Activated Acyclic Ketones.
Org Lett. 2016 Jan 15; 18(2):260-3.OL

Abstract

The first catalytic asymmetric vinylogous aldol reaction of activated allyls to activated acyclic ketones is disclosed. A variety of activated acyclic ketones, such as trifluoromethyl ketones, α-ketoesters, and α-keto phosphonates, were found to be involved forming diverse γ-selective aldol adducts with high enantioselectivities (up to >99% ee). The method provides an effective, general strategy to access valuable chiral electron-withdrawing group-substituted tertiary hydroxyl-based carboxylic acids.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Jing Z
Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University , Jinming Campus, Kaifeng, Henan 475004, China.
Bai X
Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University , Jinming Campus, Kaifeng, Henan 475004, China.
Chen W
Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University , Jinming Campus, Kaifeng, Henan 475004, China.
Zhang G
Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University , Jinming Campus, Kaifeng, Henan 475004, China.
Zhu B
Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University , Jinming Campus, Kaifeng, Henan 475004, China.
Jiang Z
Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University , Jinming Campus, Kaifeng, Henan 475004, China.

Pub Type(s)

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

Language

eng

PubMed ID

26727214

Citation

Jing, Zhenzhong, et al. "Organocatalytic Enantioselective Vinylogous Aldol Reaction of Allyl Aryl Ketones to Activated Acyclic Ketones." Organic Letters, vol. 18, no. 2, 2016, pp. 260-3.
Jing Z, Bai X, Chen W, et al. Organocatalytic Enantioselective Vinylogous Aldol Reaction of Allyl Aryl Ketones to Activated Acyclic Ketones. Org Lett. 2016;18(2):260-3.
Jing, Z., Bai, X., Chen, W., Zhang, G., Zhu, B., & Jiang, Z. (2016). Organocatalytic Enantioselective Vinylogous Aldol Reaction of Allyl Aryl Ketones to Activated Acyclic Ketones. Organic Letters, 18(2), 260-3. https://doi.org/10.1021/acs.orglett.5b03412
Jing Z, et al. Organocatalytic Enantioselective Vinylogous Aldol Reaction of Allyl Aryl Ketones to Activated Acyclic Ketones. Org Lett. 2016 Jan 15;18(2):260-3. PubMed PMID: 26727214.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Organocatalytic Enantioselective Vinylogous Aldol Reaction of Allyl Aryl Ketones to Activated Acyclic Ketones. AU - Jing,Zhenzhong, AU - Bai,Xiangbin, AU - Chen,Wenchao, AU - Zhang,Gao, AU - Zhu,Bo, AU - Jiang,Zhiyong, Y1 - 2016/01/04/ PY - 2016/1/5/entrez PY - 2016/1/5/pubmed PY - 2016/1/5/medline SP - 260 EP - 3 JF - Organic letters JO - Org Lett VL - 18 IS - 2 N2 - The first catalytic asymmetric vinylogous aldol reaction of activated allyls to activated acyclic ketones is disclosed. A variety of activated acyclic ketones, such as trifluoromethyl ketones, α-ketoesters, and α-keto phosphonates, were found to be involved forming diverse γ-selective aldol adducts with high enantioselectivities (up to >99% ee). The method provides an effective, general strategy to access valuable chiral electron-withdrawing group-substituted tertiary hydroxyl-based carboxylic acids. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/26727214/Organocatalytic_Enantioselective_Vinylogous_Aldol_Reaction_of_Allyl_Aryl_Ketones_to_Activated_Acyclic_Ketones_ DB - PRIME DP - Unbound Medicine ER -