Bidirectional Synthesis of Di-tert-butyl (2S,6S,8S)- and (2R,6R,8R)-1,7-Diazaspiro[5.5]undecane-2,8-dicarboxylate and Related Spirodiamines

被引：4

作者：

Almond-Thynne, Joshua ^{[1
]}

Han, Jiaxu ^{[1
]}

White, Andrew J. P. ^{[1
]}

Polyzos, Anastasios ^{[2
,3
]}

Parsons, Philip J. ^{[1
]}

Barrett, Anthony G. M. ^{[1
]}

机构：

[1] Imperial Coll London, Dept Chem, London SW7 2AZ, England

[2] CSIRO Mfg, Clayton, Vic 3169, Australia

[3] Univ Melbourne, Sch Chem, Melbourne, Vic 3010, Australia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 12期

基金：

英国工程与自然科学研究理事会;

关键词：

OLEFIN METATHESIS CATALYSTS; ALKALOIDS;

D O I：

10.1021/acs.joc.8b00794

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Efficient syntheses of both enantiomers of a spirodiamine diester from (L)- and (D)-aspartic acid are described. The key transformation was the conversion of Boc-protected tert-butyl aspartate into the derived aldehyde, two-directional Horner-Wadsworth-Emmons olefination, hydrogenation, and selective acid-catalyzed Boc-deprotection and spirocyclization. An alternative, two-directional approach to derivatives of 1,7-diazaspiro[5.5]undecane is described.

引用

页码：6783 / 6787

页数：5

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