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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.

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Authors+Show Affiliations

Qiu L
State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, China.
Wang Q
No affiliation info available
Lin L
No affiliation info available
Liu X
No affiliation info available
Jiang X
No affiliation info available
Zhao Q
No affiliation info available
Hu G
No affiliation info available
Wang R
No affiliation info available

MeSH

AldehydesAlkynesAminesCatalysisOrganometallic CompoundsPentanolsStereoisomerismSubstrate SpecificitySulfonamidesTosyl Compounds

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 -