87637-48-7Relevant academic research and scientific papers
A formal catalytic asymmetric synthesis of (+)-biotin with modified cinchona alkaloids
Choi,Tian,Deng
, p. 1737 - 1741 (2001)
A formal catalytic asymmetric synthesis of (+)-biotin was realized. The key steps involve a catalytic, highly enantioselective and quantitative desymmetrization of a meso cyclic anhydride followed by a one-pot chemoselective reduction to form the optically active lactone intermediate in the Goldberg - Sternbach (+)-biotin synthesis.
Chiral squaramide-mediated methanolytic desymmetrization of prochiral cyclic anhydride: A convenient approach for synthesizing roche lactone
Ding, Liang-Qian,Hong, Dan-Feng,Liu, Wen-Guang,Ma, Hui,Tan, Qing-Gang,Wang, Shi-Heng,Wu, Si-Qin,Xiong, Fei
, p. 429 - 432 (2018/09/25)
The main objective of this report was to develop an improved process for the asymmetric synthesis of (3aS, 6aR)-lactone 1, which is the key chiral intermediate of (+)-biotin. This practical and efficient process includes a novel chiral squaramide alkamine derivatives 5 mediated methanolytic desymmetrization of prochiral cyclic anhydride 3 to produce the enantiomerically enriched precursor of Roche lactone.
A family of novel bifunctional organocatalysts: Highly enantioselective alcoholysis of meso cyclic anhydrides and its application for synthesis of the key intermediate of P2X7 receptor antagonists
Yang, Hong-Jun,Xiong, Fang-Jun,Li, Jie,Chen, Fen-Er
, p. 553 - 558 (2013/07/27)
A family of novel squaramides/sulfamides based on 1,2-alkamine was developed as chiral bifunctional catalysts to promote the asymmetric alcoholysis of meso cyclic anhydrides. The hemiesters were obtained in high yield with up to 93% ee. The usefulness of this methodology was demonstrated in the asymmetric synthesis of the key intermediate of P2X7 receptor antagonists.
An improved asymmetric total synthesis of (+)-biotin via the enantioselective desymmetrization of a meso-cyclic anhydride mediated by cinchona alkaloid-based sulfonamide
Xiong, Fei,Chen, Xu-Xiang,Chen, Fen-Er
experimental part, p. 665 - 669 (2010/07/17)
The highly enantioselective total synthesis of (+)-biotin 1 via the Hoffmann-Roche lactone-thiolactone strategy has been achieved starting from cis-1,3-dibenzyl-2-imidazolidone-4,5-dicarboxylic acid 2 with an overall yield of 35%. Two contiguous stereogenic centers at C-3a and C-6a were established through a rapid cinchona alkaloid-based sulfonamide-mediated enantioselective alcoholysis of meso-cyclic anhydride 3 to afford (4S,5R)-cinnamyl hemiester 4h, the direct precursor to (3aS,6aR)-lactone 5 with high enantioselectivity. A one-pot installation of the 4-carboxybutyl side chain was accomplished by a Fukuyama coupling reaction of (3aS,6aR)-thiolactone 6 with the organozinc reagent prepared from ethyl 5-bromopentanoate.
Total synthesis of (+)-biotin via a quinine-mediated asymmetric alcoholysis of meso-cyclic anhydride strategy
Huang, Jian,Xiong, Fei,Chen, Fen-Er
, p. 1435 - 1442 (2008/12/20)
A concise asymmetric total synthesis of (+)-biotin 1 has been accomplished in which the absolute stereochemistry of C3a, C6a of 1 was established by utilizing an efficient and practical quinine-mediated asymmetric alcoholysis of meso-cyclic anhydride 2 in a single step, the C4 stereochemistry was installed by a direct stereoselective ionic hydrogenation of the thiolactol 7.
