Expedient synthesis of chiral 1,2- and 1,4-diamines: Protecting group dependent regioselectivity in direct organocatalytic asymmetric Mannich reactions
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作者:
Chowdari, Naidu S.
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机构:Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
Chowdari, Naidu S.
Ahmad, Moballigh
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机构:Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
Ahmad, Moballigh
Albertshofer, Klaus
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机构:Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
Albertshofer, Klaus
Tanaka, Fujie
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机构:Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
Tanaka, Fujie
Barbas, Carlos F., III
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机构:Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
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
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.