A General Approach to Chiral Building Blocks via Direct Amino Acid-Catalyzed Cascade Three-Component Reductive Alkylations: Formal Total Synthesis of HIV-1 Protease Inhibitors, Antibiotic Agglomerins, Brefeldin A, and (<i>R</i>)-γ-Hexanolide
作者:Dhevalapally B. Ramachary、Y. Vijayendar Reddy
DOI:10.1021/jo901799n
日期:2010.1.1
through amino acid-catalyzed TCRA reaction without racemization at the α-position to carbonyl. Direct sequential combination of the l-proline-catalyzed TCRA reaction with other reactions like cascade alkylation/ketenization/esterification (A/K/E), alkylation/ketenization/esterification/alkylation (A/K/E/A), Brønsted acid-catalyzed cascade hydrolysis/lactonization/esterification (H/L/E), hydrolysis/esterification
多催化级联(MCC)工艺用于合成高度取代的手性结构单元(2-烷基-CH-酸,2-烷基环己烷-1,3-二酮,2-烷基环戊烷-1,3-二酮和H-P酮类似物)是基于级联三组分还原烷基化(TCRA)平台提出的。在本文中,我们通过氨基酸催化的TCRA反应开发了多种CH-酸与(R)-甘油醛丙酮化物/(S)-加纳醛醛和Hantzsch酯的高收率烷基化反应,而无需在α位上消旋化为羰基。l的直接顺序组合-脯氨酸催化的TCRA反应以及其他反应,例如级联烷基化/酮化/酯化(A / K / E),烷基化/酮化/酯化/烷基化(A / K / E / A),布朗斯台德酸催化的级联水解/内酯化/酯化(H / L / E),水解/酯化(H / E),水解/氧-迈克尔/脱水(H / OM / DH)和CH-酸,手性醛,汉茨(Hantzsch)酯的罗宾逊环化(RA)重氮甲烷,甲基乙烯基酮,各种活性烯烃和乙炔以优异的非对映选择