Expedient synthesis of chiral 1,2- and 1,4-diamines: Protecting group dependent regioselectivity in direct organocatalytic asymmetric Mannich reactions

被引:127
作者
Chowdari, Naidu S.
Ahmad, Moballigh
Albertshofer, Klaus
Tanaka, Fujie
Barbas, Carlos F., III
机构
[1] Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
[2] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
[3] Scripps Res Inst, Dept Mol Biol, La Jolla, CA 92037 USA
关键词
D O I
10.1021/ol060980d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Organocatalytic asymmetric Mannich reaction of protected amino ketones with imines in the presence of an L-proline-derived tetrazole catalyst afforded diamines with excellent yields and enantioselectivities of up to 99%. The amino ketone protecting group controlled the regioselectivity of the reaction providing access to chiral 1,2-diamines from azido ketones and 1,4-diamines from phthalimido ketones.
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页码:2839 / 2842
页数:4
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