A Useful Allene for the Stereoselective Synthesis of Protected Quaternary 2-Amino-2-vinyl-1,3-diols

被引：2

作者：

Rodriguez, Aleix ^{[1
,2
]}

Ariza, Xavier ^{[1
,2
,3
]}

Contreras, Mitguel A. ^{[1
]}

Garcia, Jordi ^{[1
,2
,3
]}

Lloyd-Williams, Paul ^{[1
,2
,3
]}

Mercadal, Nerea ^{[1
]}

Sanchez, Carolina ^{[1
]}

机构：

[1] Univ Barcelona, Fac Quim, Seccio Quim Organ, Dept Quim Inorgan & Organ, E-08028 Barcelona, Spain

[2] IBUB, Barcelona 08028, Spain

[3] Inst Salud Carlos III, CIBER Fisiopatol Obesidad & Nutr CIBERobn, Madrid 28029, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 03期

关键词：

ALPHA-AMINO-ACIDS; SPHINGOSINE-1-PHOSPHATE LYASE; SPHINGOLIPID METABOLISM; SUBSTITUTED SERINES; INHIBITORS; ROUTE; DERIVATIVES;

D O I：

10.1021/acs.joc.6b02765

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of readily available allene 1 with Cy2BH followed by addition of an aldehyde led to quaternary protected 2-amino-2-vinyl-1,3-diols in high yield and excellent stereochemical purity. The choice of benzoyl as N-protecting group is critical since the observed N- to O-Bz transfer during the process prevents later undesired isomerizations in the adducts and keeps all heteroatoms protected.

引用

页码：1851 / 1855

页数：5

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