471253-33-5

Upstream product

• 150942-98-6 t-butyl lithioacetate 
• 209391-72-0 8-[Chloro-(toluene-4-sulfinyl)-methylene]-1,4-dioxa-spiro[4.5]decane 
• 540-88-5 acetic acid tert-butyl ester 

Downstream Products

• 596119-36-7 tert-butyl {8-(p-tolylsulfinyl)methyl-1,4-dioxaspiro[4.5]dec-8-yl}acetate 
• 596119-44-7 9-(p-tolylsulfanyl)-1,4,10-trioxadispiro[4.2.4.2]tetradecan-11-one 

Relevant academic research and scientific papers

A novel synthesis of carboxylic acid derivatives having a quaternary carbon at 3-position and functional groups at 4-position from 1-chlorovinyl p-tolyl sulfoxides and acetic acid esters

Addition of the lithium enolate of acetic acid esters to 1-chlorovinyl p-tolyl sulfoxides, which were derived from ketones and chloromethyl p-tolyl sulfoxide in three steps in good yields, gave carboxylic acid esters having a quaternary carbon at the 3-po

A synthesis of bicyclo[n.1.0]alkanes having tert-butyl carboxylate or acetamide moiety via the intramolecular 1,3-CH insertion of magnesium carbenoids

Treatment of 1-chlorovinyl p-tolyl sulfoxides, derived from various cyclic ketones and chloromethyl p-tolyl sulfoxide, with lithium enolate of carboxylic acid tert-butyl esters or N,N-dimethylacetamide gave adducts in high yields. The adducts were treated with ether solution of isopropylmagnesium chloride in dry toluene to give bicyclo[n.1.0]alkane derivatives having tert-butyl carboxylate or acetamide moiety on the bridgehead carbon in high to quantitative yields via magnesium carbenoid 1,3-CH insertion reaction. The 1,3-CH insertion reaction proved to be regioselective and stereospecific. The reaction mechanism and origin of the selectivity and specificity are discussed.

A versatile synthesis, including asymmetric synthesis, of bicyclo[n.1.0]alkanes from cyclic ketones via the magnesium carbenoid 1,3-CH insertion as a key reaction

Treatment of 1-chlorovinyl p-tolyl sulfoxides, which were synthesized from various cyclic ketones and chloromethyl p-tolyl sulfoxide in three steps, in high yields, with lithium enolate of tert-butyl acetate or its homologues gave the adducts in quantitative yields. The adducts were treated with isopropylmagnesium chloride in ether in dry toluene as the reaction solvent to afford bicyclo[n.1.0]alkanes in high to quantitative yields via magnesium carbenoid 1,3-CH insertion. When this method was carried out starting from unsymmetrical cyclic ketones and (R)-chloromethyl p-tolyl sulfoxide, an asymmetric synthesis of bicyclo[n.1.0]alkane was realized.

Conjugate addition of lithium ester enolates to 1-chlorovinyl p-tolyl sulfoxides: A novel synthesis of functionalized esters and lactones having a tertiary or a quaternary carbon at the β-position

Addition of the lithium ester enolates to 1-chlorovinyl p-tolyl sulfoxides, which were synthesized from chloromethyl p-tolyl sulfoxide and ketones or aldehydes, gave esters having a tertiary or a quaternary carbon at the 3-position, and chlorine and sulfi