A direct and efficient stereoconservative procedure for the selective oxidation of N-protected β-amino alcohols

被引:27
作者
Ocejo, M [1 ]
Vicario, JL [1 ]
Badía, D [1 ]
Carrillo, L [1 ]
Reyes, E [1 ]
机构
[1] Univ Basque Country, Fac Ciencias & Tecnol, Dept Quim Organ 2, E-48080 Bilbao, Spain
关键词
amino aldehydes; amino alcohols; oxidations; iodine; green chemistry;
D O I
10.1055/s-2005-871947
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient, very simple and eco-friendly procedure has been developed for the synthesis of highly enantioenriched alpha-amino aldehydes by IBX-mediated oxidation of the corresponding beta-amino alcohols. The procedure has been applied to a wide range of substrates with different side chains and protecting groups showing that the final aldehydes can be obtained in very high yields and with no racemization at the stereogenic center present in the starting compounds.
引用
收藏
页码:2110 / 2112
页数:3
相关论文
共 53 条
[1]   4-Oxoazetidine-2-carbaldehydes as useful building blocks in stereocontrolled synthesis [J].
Alcaide, B ;
Almendros, P .
CHEMICAL SOCIETY REVIEWS, 2001, 30 (04) :226-240
[2]  
ALDEHYDE, 1999, J ORG CHEM, V64, P6434
[3]  
ALDEHYDE, 1975, CHEM PHARM BULL, V23, P3081
[4]  
ALDEHYDE, 1996, J ORG CHEM, V61, P5528
[5]  
ALDEHYDE, 1996, SYNTHESIS-STUTTGART, P641
[6]  
ALDEHYDE, 1998, TETRAHEDRON-ASYMMETR, V9, P1855
[7]  
ALDEHYDE, 2000, ORG SYNTH, V77, P64
[8]   Stereospecific synthesis of a novel azetido[2,1-c][1,4]-benzodiazepine (ABD) ring system with DNA recognition potential [J].
Bose, DS ;
Srinivas, P ;
Gurjar, MK .
TETRAHEDRON LETTERS, 1997, 38 (33) :5839-5842
[9]   A mild and efficient alternative to the classical swern oxidation [J].
De Luca, L ;
Giacomelli, G ;
Porcheddu, A .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (23) :7907-7909
[10]   A very mild and chemoselective oxidation of alcohols to carbonyl compounds [J].
De Luca, L ;
Giacomelli, G ;
Porcheddu, A .
ORGANIC LETTERS, 2001, 3 (19) :3041-3043