Synthesis Of Chiral ?-hydroxy Sulfone And ?-aryl Alcohol By Two-step One-pot Method

One-pot transformation is an efficient methodology for the construction of complex and high-value compounds from relatively simple,inexpensive,and accessible raw materials.The desired products could be obtained without isolation and purification of the intermediates,minimizing production cycle and cost,saving time and resource,as well as decreasing waste.The key to success is to develop similar medium and conditions of multi-step reaction.Therefore,the reaction of conditions and catalysts are incompatible to lead to the failure of one-pot transformation.It is a difficult in this field for asymmetric tandem reaction in a one-pot reaction system.In this paper,we report a one-pot muti-component synthesis of chiral ?-hydroxysulfones from readily available terminal alkynes and sodium sulfinates via aerobic oxysulfonylation and consecutive asymmetric transfer hydrogenation in an aqueous medium,and chiral alcohols was synthesized from racemic alcohols via the oxidation and reduction of deracemization strategy in the presence of oxygen.As follows: Series ?: Transformation of terminal alkynes into Chiral Beta-Hydroxysulfone by Oxysulfonation-Asymmetric Transfer Hydrogenation tandem ReactionFor the firsr time,we have synthesized chiral alcohols from readily available terminal alkynes and sodium sulfinates via asymmetric difunctionalization strategy of alkynes in an aqueous medium.The alcohols have been synthesized by aerobic oxysulfonylation,which was catalyzed by an inexpensive low-toxic iron salt,and consecutive asymmetric transfer hydrogenation.A variety of ?-hydroxysulfones was obtained in good yields and up to 99.9% ee values.The practical potential of this one-pot process was also demonstrated by a gram-scale synthesis.Series ?: Synthesis of Chiral Alcohols by Oxygen-Redox Deracemization StrategyRacemic alcohols as a starting material was oxidated by oxygen in dipropylene glycol dimethyl ether.The intermediation of ketone,which was subsequently reduced by a Ru-catalyzed asymmetric transfer hydrogenation with sodium formate as a hydrogen source,gives the corresponding optically active alcohols.The redox series reaction was successfully realized in one pot reaction system.