Deuterium as a Stereochemically Invisible Blocking Group for Chiral Ligand Synthesis

被引：19

作者：

Arthurs, Ross A. ^{[1
]}

Richards, Christopher J. ^{[1
]}

机构：

[1] Univ East Anglia, Sch Chem, Norwich Res Pk, Norwich NR4 7TU, Norfolk, England

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 03期

基金：

英国工程与自然科学研究理事会;

关键词：

TRANSFER HYDROGENATION; PLANAR CHIRALITY; DIPHENYLPHOSPHINO(OXAZOLINYL)FERROCENE LIGANDS; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC HYDROGENATION; RUTHENIUM COMPLEXES; CATALYSTS; EFFICIENT; KETONES; ORGANOLITHIUMS;

D O I：

10.1021/acs.orglett.6b03874

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly diastereoselective lithiation (s-BuLi/TMEDA ix Et2O, -78 degrees C, 2 h) of (5)-2-ferroceny1-4-(substituted)-oxazolines followed by addition of MeOH-d(4) gave up to 95% D incorporation. Subsequent application of alternative lithiation conditions (n-BuLi in THF, -78 degrees C, 2 h), followed by addition of an electrophile, resulted in a reversal of diastereoselectivity controlled primarily by the high k(H)/k(D) value for lithiation (isomer ratio typically between 10:1 and 20:1).

引用

页码：702 / 705

页数：4

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