手性合成英文_2.pptxVIP

Elias J. Corey－－Autobiography19281944195019561959born in Methuen，Massachusetts entered M.I.T.参与合成青霉素 completed doctoral workjoined University of Illinois became Professor of Chemistry work in Harvard 1957年Elias J. Corey 提出了他的想法：The Logic of Chemical Synthesisretrosynthetic analysis逆合成法 The logic of chemical synthesis简单的原料复杂的分子synthesistransform反合成分析法 retrosynthetic analysis retrosynthetic analysis Retrosynthetic tree树枝－－原料Best Choice?树根－－目标分子 位置控制保护基活化基桥连因子 To build left- or right handed molecules Herbert C. BrownUSAPurdue University West Lafayette, IN, USA1912 - Georg WittigFederal Republic of GermanyUniversity of Heidelberg Heidelberg, Germany1897 - 1987 The Nobel Prize in Chemistry 1979Laureates: Herbert C. BrownGeorg Wittig for their development of the use of boron- and phosphorus- containing compounds, respectively, into important reagents in organic synthesis Boron compoundsHerbert C Brownsodium boro-hydride(硼氢化钠) -- the reagent of choice for reduction of carbonyl compoundsOrganoboranes(B2H6)(the most versatile reagents ever created in organic chemistry) can be used for reductions, rearrangements and additions and have opened up a range of new possibilities for linking carbon atoms to each other.还原 重排 加成 Wittig reactionorganic phosphorus compound with aformal double bond(含双键的有机磷化合物，双键在P和C之间) between phosphorusand carbon react with a carbonyl compound(羰基化合物).The oxygen of the carbonyl compound is exchanged for carbon, the product being an olefin(烯烃)。 A carbonyl compound(羰基化合物)这是我们熟悉的Wittig试剂，用于双键化合物的制备organic phosphorus compound with a formal double bond between phosphorus and carbonolefin (烯烃) Fig 1Fig. 1. Formation of a diradical被削弱的C-C键 demetalization有机金属锂化合物diradical Formation and characterization of compound 9zinc dust distillation. 芳基质子作为取代基的不稳定性惊人发现：umpolung 规则或极性逆转规则F 的特异性 Reversal of polarity (umpolung)极性逆转 Mechanism of formation of o-lithiobiphenyl Proof of the intermediate occurrence of dehydrobenzene in the reaction of 14 C-labeled chl