New Synthesis of Poly(S-thioester)s by Regioselective Addition Reaction of Bis(thiirane)s with Diacyl Chlorides Using Quaternary Onium Salts

1997 ◽  
Vol 30 (21) ◽  
pp. 6494-6497 ◽  
Author(s):  
Atsushi Kameyama ◽  
Yasuhiro Kimura ◽  
Tadatomi Nishikubo
Keyword(s):  
Addition Reaction ◽  
Onium Salts ◽  
New Synthesis ◽  
Regioselective Addition

Synthesis of reactive polyesters by a regioselective addition reaction of diepoxides with diacyl chlorides and their chemical modification

1992 ◽  
Vol 25 (9) ◽  
pp. 2307-2311 ◽  
Author(s):  
Atsushi Kameyama ◽  
Shoji Watanabe ◽  
Eiichiro Kobayashi ◽  
Tadatomi Nishikubo
Keyword(s):  
Chemical Modification ◽  
Addition Reaction ◽  
Regioselective Addition

Spacer-modified polymeric catalysts containing phosphonium salts for a regioselective addition reaction of epoxy compounds with active esters

1990 ◽  
Vol 23 (14) ◽  
pp. 3406-3411 ◽  
Author(s):  
Tadatomi Nishikubo ◽  
Tetsuya Kato ◽  
Yoriatsu Sugimoto ◽  
Masao Tomoi ◽  
Satoshi Ishigaki
Keyword(s):  
Addition Reaction ◽  
Phosphonium Salts ◽  
Active Esters ◽  
Regioselective Addition

A short enantioselective synthesis of 3-epi-jaspine B and (+)-oxybiotin via an intramolecular tandem desilylation oxa-Michael addition strategy

RSC Advances ◽  
2014 ◽  
Vol 4 (91) ◽  
pp. 49770-49774 ◽  
Author(s):  
Anil M. Shelke ◽  
Varun Rawat ◽  
Arumugam Sudalai ◽  
Gurunath Suryavanshi
Keyword(s):  
Michael Addition ◽  
Addition Reaction ◽  
Enantioselective Synthesis ◽  
Asymmetric Epoxidation ◽  
Michael Addition Reaction ◽  
New Synthesis ◽  
Sharpless Asymmetric Epoxidation ◽  
Jaspine B

A new synthesis of cytotoxic 3-epi-jaspine B (34.7% overall yield; 97% ee) and (+)-oxybiotin (21.2% overall yield; 97% ee) is described starting from cis-2-butene-1,4-diol. The key reactions employed in the synthesis are Sharpless asymmetric epoxidation and a novel tandem desilylation-oxa Michael addition reaction.

Synthesis of a new photoreactive polyester by addition reaction of bisepoxide with f-truxiloyl chloride and chemical modification of this polymer

1995 ◽  
Vol 7 (3) ◽  
pp. 245-254 ◽  
Author(s):  
Tadatomi Nishikubo ◽  
Atsushi Kameyama ◽  
Nobuyuki Hayashi ◽  
Riou Nakagome
Keyword(s):  
Cinnamic Acid ◽  
Main Chain ◽  
Addition Reaction ◽  
Diglycidyl Ether ◽  
Substitution Reactions ◽  
Photosensitive Polymers ◽  
Onium Salts ◽  
Working Groups ◽  
Ester Moiety ◽  
Cyclobutane Ring

A new reactive polyester (P-I) containing a cyclobutane ring in the main chain and a pendant chloromethyl group in the side chain was synthesized successfully by the addition reaction of diglycidyl ether of bisphenol A (DGEBA) with fi-truxiloyl chloride (TC). The addition reaction of DGEBA with TC proceeded smoothly to give P-1 with a relatively high molecular weight using quaternary onium salts or a crown ether complex as catalysts at 90-C for 15 h. However, the reaction did not occur without a catalyst. Substitution reactions of the obtained P-I with (4-dimethy Iamino)cinnamic acid (MACA), [(4-dimethylamino)-a-cyano]cinnamic acid (MACCA) and (4-dimethylamino4'-hydroxy)chalcone (MACH) were carried out to synthesize certain new multifunctiqnal photosensitive polymers with positive-working groups in the main chain and negative-working groups in the side chains. The reaction of P-I with MACA proceeded very smoothly with 99% conversion to form the corresponding polymer (P-2a) using 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) as a base in DMF. The reaction with MACCA gave the corresponding polymer (P-2b) containing a pendant [(4-dimethylamino)-a-cyano]cinnamJc ester moiety with 26% conversion. The reaction with MIACH produced the corresponding polymer (P-2c) containing a pendant (4-dimethy]amino)chalcone ether moiety with 32% conversion. Photochernical reaction of the thus-obtained P-2a-c was also performed in the film state.

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