First synthesis of optically pure α-amino amine as asymmetric amino transfer reagent and its use in asymmetric Mannich reaction
✍ Scribed by Yoshishiro Matsumura; Takashi Tomita
- Book ID
- 104214310
- Publisher
- Elsevier Science
- Year
- 1994
- Tongue
- French
- Weight
- 288 KB
- Volume
- 35
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
An optically pun aeamim amine was first synthesized fiom Glysine utilizing anodic oxidatim as a key step. andi~usefulnesswasexemplifiedbythcasymmetricMannichreactientogiveopticallyectiveBaminoacid tsters. Asymmetric tmnsfcr of amino group frwm amines substituted with chiral auxiky is a convenient synthetic route to new optically active amino compounds' but there have been few methoda to fulfill some conditions descritxd below which would make this route mum convenient. Namely, it is desirable from a synthetic viewpuint thatstattiagqicallyactiveamincsa!J -damtrolpoupamcasilyavailableufcanbcprepaFcdwithcanplete opticalpurity, theaminolransfcrmactiontakcsplacecfCciently, thexemovalofchiralauxikyiseasilyachievablc bysimpIe~ratthelaterseageofthemursferrtactionsequence, andthechiralauxikyisrecovuedaftc.r the amino tmnsfer reaction. Such amino transfer reagents t~%~tly exploited m a-oxo aminer 1 such'as Oprotected glycosylamines.* On view of the successful tesulta using 1, a-amino amines 2, N-analogues of 1,