Boesten W H, Seerden J P, de Lange B, Dielemans H J, Elsenberg H L, Kaptein B, Moody H M, Kellogg R M, Broxterman Q B
DSM Research Life Sciences-Organic Chemistry and Biocatalysis, P.O. Box 18, 6160 MD Geleen, and Syncom B.V., Kadijk 3, 9747 AT Groningen, The Netherlands.
Org Lett. 2001 Apr 19;3(8):1121-4. doi: 10.1021/ol007042c.
[reaction: see text]. Diastereoselective Strecker reactions based on (R)-phenylglycine amide as chiral auxiliary are reported. The Strecker reaction is accompanied by an in situ crystallization-induced asymmetric transformation, whereby one diastereomer selectively precipitates and can be isolated in 76-93% yield and dr > 99/1. The diastereomerically pure alpha-amino nitrile obtained from pivaldehyde (R1 = t-Bu, R2 = H) was converted in three steps to (S)-tert-leucine in 73% yield and >98% ee.
[反应：见正文]。报道了以（R）-苯甘氨酸酰胺为手性助剂的非对映选择性施特雷克反应。施特雷克反应伴随着原位结晶诱导的不对称转化，其中一种非对映体选择性沉淀，可分离得到，产率为76 - 93%，非对映体过量值（dr）> 99/1。由新戊醛（R1 =叔丁基，R2 =氢）得到的非对映体纯的α-氨基腈经三步反应转化为（S）-叔亮氨酸，产率为73%，对映体过量值（ee）> 98%。
