Highly Enantio- and Diastereoselective Allylic Alkylation of Morita–Baylis–Hillman Carbonates with Allyl Ketones
The Journal of Organic Chemistry2013Vol. 78(10), pp. 5067–5072
Citations Over TimeTop 15% of 2013 papers
Guanghu Tong, Bo Zhu, Richmond Lee, Wenguo Yang, Davin Tan, Caiyun Yang, Zhiqiang Han, Lin Yan, Kuo‐Wei Huang, Zhiyong Jiang
Abstract
The asymmetric allylic alkylation of Morita-Baylis-Hillman (MBH) carbonates with allyl ketones has been developed. The α-regioselective alkylation adducts, containing a hexa-1,5-diene framework with important synthetic value, were achieved in up to 83% yield, >99% ee, and 50:1 dr by using a commercially available Cinchona alkaloid as the catalyst. From the allylic alkylation adduct, a cyclohexene bearing two adjacent chiral centers was readily prepared.
Related Papers
- → Transition metal-catalyzed allylic substitution reactions with unactivated allylic substrates(2015)668 cited
- → Metal-catalyzed rearrangements of allylic esters(1984)59 cited
- → One-Pot Synthesis of Homoallylic Alcohols via a Facile Conversion of Allylic Alcohols into Allylic Iodides(1989)30 cited
- → ChemInform Abstract: Allylic Selenides in Organic Synthesis: New Methods for the Synthesis of Allylic Amines.(1987)
- → Synthesis of chiral 2,2$prime;-dipyridylamines and their use in the copper-catalyzed asymmetric allylic oxidation of cyclohexene(2004)