Reversal of diastereofacial selectivity in the nucleophilic addition reaction to chiral N-sulfinimine and application to the synthesis of indrizidine 223AB
Reversal of diastereofacial selectivity in the nucleophilic addition reaction to chiral N-sulfinimine and application to the synthesis of indrizidine 223AB
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DOI：
10.1016/s0040-4020(02)01250-4
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发表时间：
2002-11-18
期刊：
影响因子：
2.1
通讯作者：
Shimizu, M
中科院分区：
文献类型：
--
作者：
Koriyama, Y;Nozawa, A;Shimizu, M
研究了烯醇化酯与格氏试剂对光学活性N-亚磺酰亚胺的非对映选择性加成反应。通过选择合适的金属物种、溶剂和添加剂，实现了对非对映选择性的抑制，并以良好的产率获得了β-氨基酯（高达>98% de）和高烯丙基胺（高达>98% de）。将由此获得的β-氨基酯转化为包括（R）-高丝氨酸的有用的β-氨基酸。并介绍了其在吲哚里西啶生物碱合成中的应用。(C)2002年由Elsevier Science Ltd.出版
Diastereoselective addition reaction of ester enolates and Grignard reagents to optically active N-sulfinimines was examined. Reversal of the diastereofacial selectivity was realized by using appropriate metal species, solvents and additives, and the beta-amino esters (up to >98% de) and the homoallylic amines (up to >98% de) were obtained in good yields. beta-Amino esters thus obtained were converted to the useful beta-amino acids involving (R)-homoserine. Application to the synthesis of indrizidine alkaloids was also described. (C) 2002 Published by Elsevier Science Ltd.