1206227-45-3Relevant academic research and scientific papers
Synthesis method for tert-butyl 1,2,3-oxathiazolidine-3-carboxylic ester 2,2-dioxide compound
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Paragraph 0041-0047; 0181-0187, (2020/07/13)
The invention relates to a synthesis method for a tert-butyl 1,2,3-oxathiazolidine-3-carboxylic ester 2,2-dioxide compound. The tert-butyl 1,2,3-oxathiazolidine-3-carboxylic ester 2,2-dioxide compoundhas a structural formula as shown in a formula I which is described in the specification. The synthesis method comprises the step of allowing a compound as shown in a formula II which is described inthe specification with sulfonyl chloride in the presence of an organic solvent to generate the compound as shown in the formula I. The structural formula of the compound as shown in the formula I andthe structural formula of the compound as shown in the formula II are described in the specification. The synthesis method disclosed by the invention is simple to operate; compared with a conventional published two-step method, the synthesis method provided by the invention only needs one step; and the synthesis method is more convenient, reduces byproducts, is high in yield, does not need to usea catalyst and a highly-toxic substance in the reaction, and is safe and low in cost.
Tunable Bifunctional Phosphine-Squaramide Promoted Morita-Baylis-Hillman Reaction of N-Alkyl Isatins with Acrylates
Dong, Ze,Yan, Chao,Gao, Yongzhi,Dong, Chune,Qiu, Guofu,Zhou, Hai-Bing
, p. 2132 - 2142 (2015/06/23)
A series of highly tunable bifunctional phosphine-squaramide H-bond donor organocatalysts 6 has been synthesized from inexpensive and commercially available β-amino alcohols in moderate yields. Catalyst 6 can efficiently promote the asymmetric Morita-Baylis-Hillman (MBH) reaction of N-alkyl isatins with acrylate esters providing the chiral 3-substituted 3-hydroxy-2-oxindoles in good yields and enantioselectivities (up to 93 yield and 95 ee), in which the challenging substrate tert-butyl acrylate 9d, provided the best ee value to date. Moreover, this methodology was applied successfully in the synthesis of chiral cyclic spiropyrrolizidineoxindole and γ-butyrolactone derivatives without enantioselectivity deterioration. The possible mechanism of this MBH reaction was also investigated by 31PNMR, ESI-MS and KIE studies. The KIE experiments show that the electrophilic addition of N-methyl isatin to the complex of acrylate ester and phophine-squaramide is the rate-determing step of the asymmetric MBH reaction.
Synthesis of chiral aminophosphines from chiral aminoalcohols via cyclic sulfamidates
Guo, Rongwei,Lu, Shuiming,Chen, Xuanhua,Tsang, Chi-Wing,Jia, Wenli,Sui-Seng, Christine,Amoroso, Dino,Abdur-Rashid, Kamaluddin
supporting information; experimental part, p. 937 - 940 (2010/05/02)
(Chemical Equation Presented) Protic aminophosphines with multiple chiral centers were synthesized in good yields and high purity by the nucleophilic ring-opening of N-protected cyclic sulfamidates with metal phosphides, followed by hydrolysis and deprote
