Evaluation of the Efficiency of the Chiral Quaternary Ammonium Salt β-Np-NAS-Br in the Organic-Aqueous Phase-Transfer Alkylation of a Protected Glycine Derivative
Evaluation of the Efficiency of the Chiral Quaternary Ammonium Salt β-Np-NAS-Br in the Organic-Aqueous Phase-Transfer Alkylation of a Protected Glycine Derivative
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DOI：
10.1002/1615-4169(200206)344:3/4
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发表时间：
2002-06
影响因子：
5.4
通讯作者：
T. Ooi;Y. Uematsu;K. Maruoka
中科院分区：
文献类型：
--
作者：
T. Ooi;Y. Uematsu;K. Maruoka
研究了N-螺环C2对称手性季铵盐（S，S）-3 [（S，S）-β-Np-NAS-Br]在甘氨酸叔丁酯二苯甲酮Schiff碱（1）的典型有机-水相转移苄基化和烯丙基化反应中的固有效率。这揭示了天然和非天然α-氨基酸的不对称合成的实际条件，其有用性已通过抗生素L-氮杂酪氨酸的形式对映选择性合成得到证实。
The inherent efficiency of the N-spiro C2-symmetric chiral quaternary ammonium salt (S,S)-3 [(S,S)-β-Np-NAS-Br] has been evaluated in the representative organic-aqueous liquid-liquid phase-transfer benzylation and allylation of glycine tert-butyl ester benzophenone Schiff base (1). This revealed the practical conditions for the asymmetric synthesis of both natural and unnatural α-amino acids, whose usefulness was demonstrated by the formal enantioselective synthesis of antibiotic L-azatyrosine.