Yong-Hong Chen's research while affiliated with Nankai University and other places
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Publications (2)
Herein, we report the first enantioselective total synthesis of the highly complex hamigeran diterpenoid (-)-hamigeran F and its rearrangement product. The synthetic strategy features key steps of asymmetric hydrogenation, Horner-Wadsworth-Emmons olefination, and intramolecular Friedel-Crafts acylation to construct the [6,6,5]-tricyclic skeleton be...
Citations
... In addition, the asymmetric hydrogenation of racemic α-aryl-β-ethoxycarbonyl cyclopentanones via DKR for the synthesis of chiral cyclopentanols with three contiguous stereocenters was also demonstrated by Xie [76] et al. This reaction was successfully used for the synthesis of natural products such as (+)-burmaniol A, (À )hamigeran B [77] and (À )-hamigeran F. [78] Interestingly, when the α,β-unsaturated β'-keto esters 48 [79] were used as substrates in the iridium-SpiroPAP L3a catalyzed asymmetric hydrogenation (Scheme 40), the C=O and C=C bonds were hydrogenated sequentially in a single step, giving the corresponding chiral cyclic alcohols 49 bearing three contiguous stereocenters with excellent enantioselec-tivities (92 to > 99% ee) and diastereoselectivities (dr 95/5 to > 99/1). The main reason for this unexpected result was that the electron-withdrawing α-ester group polarized the C=C bond, making it more susceptible to hydrogenation. ...
![[object Object]](https://c5.rgstatic.net/m/4671872220764/images/template/default/profile/profile_default_m.jpg)
... With the chiral spiro iridium catalyst, Ir-SpiroPAP L3, a series of exocyclic γ,δ-unsaturated βketo esters containing a five-, six-, or seven-membered ring 46 were hydrogenated to the corresponding chiral allylic alcohols 47 in high yields with good to excellent enantioselectivities (87 to > 99% ee) and cis-selectivities (93:7 to > 99:1) (Scheme 39). In addition, the asymmetric hydrogenation of racemic α-aryl-β-ethoxycarbonyl cyclopentanones via DKR for the synthesis of chiral cyclopentanols with three contiguous stereocenters was also demonstrated by Xie [76] et al. This reaction was successfully used for the synthesis of natural products such as (+)-burmaniol A, (À )hamigeran B [77] and (À )-hamigeran F. [78] Interestingly, when the α,β-unsaturated β'-keto esters 48 [79] were used as substrates in the iridium-SpiroPAP L3a catalyzed asymmetric hydrogenation (Scheme 40), the C=O and C=C bonds were hydrogenated sequentially in a single step, giving the corresponding chiral cyclic alcohols 49 bearing three contiguous stereocenters with excellent enantioselec-tivities (92 to > 99% ee) and diastereoselectivities (dr 95/5 to > 99/1). ...
