116199-45-2

Upstream product

• 2344-70-9 (R)-4-phenyl-2-butanol 
• 137029-98-2 (R)-N-(p-toluenesulfonyl)-1-methyl-3-phenylpropylamine 
• 22374-89-6 (RS)-1-methyl-3-phenylpropylamine 
• 937-52-0 (R)-1-methyl-3-phenylpropylamine 
• 153357-82-5 (R)-N,N-di-(p-toluenesulfonyl)-1-methyl-3-phenylpropylamine 
• 2344-70-9 (+)-(S)-4-phenylbutan-2-ol 

Downstream Products

• 4187-57-9 (S)-1-methyl-3-phenylpropylamine 

Relevant academic research and scientific papers

One-Pot Deoxygenation and Substitution of Alcohols Mediated by Sulfuryl Fluoride

Sulfuryl fluoride is a valuable reagent for the one-pot activation and derivatization of aliphatic alcohols, but the highly reactive alkyl fluorosulfate intermediates limit both the types of reactions that can be accessed as well as the scope. Herein, we report the SO2F2-mediated alcohol substitution and deoxygenation method that relies on the conversion of fluorosulfates to alkyl halide intermediates. This strategy allows the expansion of SO2F2-mediated one-pot processes to include radical reactions, where the alkyl halides can also be exploited in the one-pot deoxygenation of primary alcohols under mild conditions (52-95% yield). This strategy can also enhance the scope of substitutions to nucleophiles that are previously incompatible with one-pot SO2F2-mediated alcohol activation and enables substitution of primary and secondary alcohols in 54-95% yield. Chiral secondary alcohols undergo a highly stereospecific (90-98% ee) double nucleophilic displacement with an overall retention of configuration.

Two-Step Protocol for Iodotrimethylsilane-Mediated Deoxy-Functionalization of Alcohols

We have developed a two-step protocol for iodotrimethylsilane-mediated deoxy-functionalization of primary and secondary alcohols to afford products containing a C?N, C?S, or C?O bond. In the first step the alcohol undergoes iodination with iodotrimethylsilane, and in the second, the iodine atom is replaced by a N, S, or O nucleophile. Compared with traditional Mitsunobu reaction, non-acidic pre-nucleophiles can be used, and the reaction proceeds with retention of configuration. This operationally simple, highly efficient protocol can be used for some natural products and small-molecule drugs containing hydroxy-group.

A new type of oxidation-reduction condensation by the combined use of phenyl diphenylphosphinite and oxidant

A new type of oxidation-reduction condensation of alcohols with sulfur, nitrogen, and oxygen nucleophiles by the combined use of phenyl diphenylphosphinite (PhOPPh2) and oxidants such as azides or diethyl azodicarboxylate (DEAD) are described. In these reactions, chiral secondary and tertiary alcohols are converted into the corresponding chiral sulfides, azides, esters and ethers under mild and neutral conditions with almost complete inversion of stereochemical configuration.

Stereospecific synthesis of sec- and tert-alkyl azides from alcohols and trimethylsilyl azide by a new type of oxidation-reduction condensation using phenyl diphenylphosphinite and trimethylsilylmethyl azide

A novel method for the preparation of alkyl azides from alcohols and trimethylsilyl azide by a new type of oxidation-reduction condensation using phenyl diphenylphosphinite and trimethylsilylmethyl azide is described. Chiral secondary and tertiary alcohols are converted into the corresponding chiral azides with almost complete inversion of configuration under mild and neutral conditions. Copyright

Stereoselective transformation of amines via chiral 2,4,6-triphenylpyridinium intermediates

We herein report the preparation and the nucleophilic substitution of the chiral 2,4,6-triphenylpyridinium tetrafluoroborates 2a and 2b. The triphenylpyridinium intermediates were generated from homochiral amines (1a, 1b) and 2,4,6-triphenylpyrylium tetrafluoroborate and used as substrates for stereoselective nucleophilic substitution. The degree of inversion in the substitution reactions has been studied. The alcohol (3a, 3b) and azide (4a, 4b) products were obtained with >99 and 96-98% inversion of configuration, respectively.