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Highly enantioselective addition of terminal alkynes to aldehydes catalyzed by a new chiral beta-sulfonamide alcohol/Ti(OiPr)4/Et2Zn/R3N catalyst system.
Chirality. 2009 Feb; 21(2):316-23.C

Abstract

A new catalytic system, generated from the readily available and inexpensive beta-sulfonamide alcohol L*, Ti(O(i)Pr)(4), Et(2)Zn, and tertiary amine base (R(3)N), effectively catalyzes the enantioselective addition of various terminal alkynes including some quite challenging alkynes to aldehydes in good yields and excellent enantioselectivities. Up to 96% yield and >99% enantioselectivity were achieved with the use of N,N-diisoproylethylamine (DIPEA) as an additive in this asymmetric addition.

Authors+Show Affiliations

State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, China.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

18537166

Citation

Qiu, Li, et al. "Highly Enantioselective Addition of Terminal Alkynes to Aldehydes Catalyzed By a New Chiral Beta-sulfonamide alcohol/Ti(OiPr)4/Et2Zn/R3N Catalyst System." Chirality, vol. 21, no. 2, 2009, pp. 316-23.
Qiu L, Wang Q, Lin L, et al. Highly enantioselective addition of terminal alkynes to aldehydes catalyzed by a new chiral beta-sulfonamide alcohol/Ti(OiPr)4/Et2Zn/R3N catalyst system. Chirality. 2009;21(2):316-23.
Qiu, L., Wang, Q., Lin, L., Liu, X., Jiang, X., Zhao, Q., Hu, G., & Wang, R. (2009). Highly enantioselective addition of terminal alkynes to aldehydes catalyzed by a new chiral beta-sulfonamide alcohol/Ti(OiPr)4/Et2Zn/R3N catalyst system. Chirality, 21(2), 316-23. https://doi.org/10.1002/chir.20583
Qiu L, et al. Highly Enantioselective Addition of Terminal Alkynes to Aldehydes Catalyzed By a New Chiral Beta-sulfonamide alcohol/Ti(OiPr)4/Et2Zn/R3N Catalyst System. Chirality. 2009;21(2):316-23. PubMed PMID: 18537166.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Highly enantioselective addition of terminal alkynes to aldehydes catalyzed by a new chiral beta-sulfonamide alcohol/Ti(OiPr)4/Et2Zn/R3N catalyst system. AU - Qiu,Li, AU - Wang,Quan, AU - Lin,Li, AU - Liu,Xiaodong, AU - Jiang,Xianxing, AU - Zhao,Qingyang, AU - Hu,Guowen, AU - Wang,Rui, PY - 2008/6/10/pubmed PY - 2009/2/20/medline PY - 2008/6/10/entrez SP - 316 EP - 23 JF - Chirality JO - Chirality VL - 21 IS - 2 N2 - A new catalytic system, generated from the readily available and inexpensive beta-sulfonamide alcohol L*, Ti(O(i)Pr)(4), Et(2)Zn, and tertiary amine base (R(3)N), effectively catalyzes the enantioselective addition of various terminal alkynes including some quite challenging alkynes to aldehydes in good yields and excellent enantioselectivities. Up to 96% yield and >99% enantioselectivity were achieved with the use of N,N-diisoproylethylamine (DIPEA) as an additive in this asymmetric addition. SN - 1520-636X UR - https://www.unboundmedicine.com/medline/citation/18537166/Highly_enantioselective_addition_of_terminal_alkynes_to_aldehydes_catalyzed_by_a_new_chiral_beta_sulfonamide_alcohol/Ti_OiPr_4/Et2Zn/R3N_catalyst_system_ L2 - https://doi.org/10.1002/chir.20583 DB - PRIME DP - Unbound Medicine ER -