Ding, Pei-Gang; Zhou, Feng; Wang, Xin; Zhao, Qiu-Hua; Yu, Jin-Sheng; Zhou, Jian published the artcile< H-bond donor-directed switching of diastereoselectivity in the Michael addition of α-azido ketones to nitroolefins>, SDS of cas: 112-63-0, the main research area is nitroalkene azido ketone bifunctional chiral amide catalyst Michael addition; azido nitroalkanone preparation diastereoselective enantioselective.
The potency of H-bond donors as the governing factor to tune diastereoselectivity in a highly diastereoselective switchable enantioselective Michael addition of α-azido ketones to nitroolefins was reported. While a newly developed bifunctional tertiary amine, phosphoramide, preferentially afforded syn-adducts, an analogous squaramide catalyst selectively gave anti-adducts. The resulting multifunctional tertiary azides were converted to spiro-pyrrolidines with four continuous stereocenters in a one-pot operation. Mechanistic studies casted light on the control of diastereoselectivity by H-bond donors. While the squaramide-catalyzed reaction proceeded with a transition state with both squaramide N-H bonds binding to an enolate intermediate, an unprecedented model was proposed for the phosphoramide-mediated reaction wherein an amide N-H bond and an alkylammonium ion formed in-situ interacted with nitroolefins, with the enolate stabilized by non-classical C-H···O hydrogen-bonding interactions.
Chemical Science published new progress about Alkanes, nitro Role: PRP (Properties), RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 112-63-0 belongs to class esters-buliding-blocks, and the molecular formula is C19H34O2, SDS of cas: 112-63-0.
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics