Organocatalytic Enantioselective [1 + 4] Annulation of Morita-Baylis-Hillman Carbonates with Electron-Deficient Olefins: Access to Chiral 2,3-Dihydrofuran Derivatives.Org Lett. 2017 09 15; 19(18):4774-4777.OL
Abstract
A reaction has been developed for the chiral phosphine-catalyzed enantioselective [1 + 4] annulation of Morita-Baylis-Hillman carbonates with electron-deficient olefins via a Michael alkylation process. Morita-Baylis-Hillman carbonates reacted smoothly with β,γ-unsaturated α-keto ester and α,β-unsaturated ketone substrates under 1,2-bis[(2R,5R)-2,5-dimethylphospholano]benzene monoxide catalysis to furnish a wide range of optically active 2,3-dihydrofurans in high yields (up to 95%) with excellent asymmetric induction (up to >99% ee, >20:1 dr). This protocol represents an efficient strategy for the synthesis of optically active multifunctional 2,3-dihydrofurans via an asymmetric Michael alkylation domino reaction.
Links
Pub Type(s)
Journal Article
Research Support, Non-U.S. Gov't
Language
eng
PubMed ID
28846432
Citation
Cheng, Yuyu, et al. "Organocatalytic Enantioselective [1 + 4] Annulation of Morita-Baylis-Hillman Carbonates With Electron-Deficient Olefins: Access to Chiral 2,3-Dihydrofuran Derivatives." Organic Letters, vol. 19, no. 18, 2017, pp. 4774-4777.
Cheng Y, Han Y, Li P. Organocatalytic Enantioselective [1 + 4] Annulation of Morita-Baylis-Hillman Carbonates with Electron-Deficient Olefins: Access to Chiral 2,3-Dihydrofuran Derivatives. Org Lett. 2017;19(18):4774-4777.
Cheng, Y., Han, Y., & Li, P. (2017). Organocatalytic Enantioselective [1 + 4] Annulation of Morita-Baylis-Hillman Carbonates with Electron-Deficient Olefins: Access to Chiral 2,3-Dihydrofuran Derivatives. Organic Letters, 19(18), 4774-4777. https://doi.org/10.1021/acs.orglett.7b02144
Cheng Y, Han Y, Li P. Organocatalytic Enantioselective [1 + 4] Annulation of Morita-Baylis-Hillman Carbonates With Electron-Deficient Olefins: Access to Chiral 2,3-Dihydrofuran Derivatives. Org Lett. 2017 09 15;19(18):4774-4777. PubMed PMID: 28846432.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR
T1 - Organocatalytic Enantioselective [1 + 4] Annulation of Morita-Baylis-Hillman Carbonates with Electron-Deficient Olefins: Access to Chiral 2,3-Dihydrofuran Derivatives.
AU - Cheng,Yuyu,
AU - Han,Yuzhe,
AU - Li,Pengfei,
Y1 - 2017/08/28/
PY - 2017/8/29/pubmed
PY - 2017/8/29/medline
PY - 2017/8/29/entrez
SP - 4774
EP - 4777
JF - Organic letters
JO - Org Lett
VL - 19
IS - 18
N2 - A reaction has been developed for the chiral phosphine-catalyzed enantioselective [1 + 4] annulation of Morita-Baylis-Hillman carbonates with electron-deficient olefins via a Michael alkylation process. Morita-Baylis-Hillman carbonates reacted smoothly with β,γ-unsaturated α-keto ester and α,β-unsaturated ketone substrates under 1,2-bis[(2R,5R)-2,5-dimethylphospholano]benzene monoxide catalysis to furnish a wide range of optically active 2,3-dihydrofurans in high yields (up to 95%) with excellent asymmetric induction (up to >99% ee, >20:1 dr). This protocol represents an efficient strategy for the synthesis of optically active multifunctional 2,3-dihydrofurans via an asymmetric Michael alkylation domino reaction.
SN - 1523-7052
UR - https://www.unboundmedicine.com/medline/citation/28846432/Organocatalytic_Enantioselective_[1_+_4]_Annulation_of_Morita_Baylis_Hillman_Carbonates_with_Electron_Deficient_Olefins:_Access_to_Chiral_23_Dihydrofuran_Derivatives_
L2 - https://doi.org/10.1021/acs.orglett.7b02144
DB - PRIME
DP - Unbound Medicine
ER -
