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首页> 外文期刊>Chemistry: A European journal >Mono- and disubstituted Nu,Nu-dialkylcyclopropylamines from dialkylformamides via ligand-exchanged titanium-alkene complexes
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Mono- and disubstituted Nu,Nu-dialkylcyclopropylamines from dialkylformamides via ligand-exchanged titanium-alkene complexes

机译：二烷基甲酰胺经配体交换的钛-烯烃络合物单和双取代的Nu，Nu-二烷基环丙胺

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摘要

Dibenzylformamide was treated with cyclohexylmagnesium bromide in the presence of either titanium tetraisopropoxide or methyltitanium triisopropoxide and a variety of cyclic and acyclic alkenes and alkadienes to give new mono- and disubstituted as well as bicyclic dialkylcyclopropylamines (Tables 1-3) in yields ranging from 18 to 90 % (in most cases around 55%). 3-Benzyl-6-(N,N'-dibenzylamino)-3-azabicyclo[3.1.0]hexane (10 a) and the orthogonally bisprotected 3-tert-butoxycarbonyl-6-(N,N-dibenzyl)-3-azabicyclo[3.1.0]hexane (10d) as well as the analogous 6-(N,N-dibenzylamino)bicyclo[3.1.0]hexane (12) were obtained as pure exo diastereomers in particularly high yields (87, 90, and 88 %, respectively) from N-benzylpyrroline (15a), N-Boc-pyrroline (15d; Boc=tert-butyloxycarbonyl) and cyclopentene (19). 1,3-Butadiene (52) and substituted 1,3-butadienes were also aminocyclopropanated quite well to give 2-ethenylcyclopropylamines in good yields (51-64%). Except for alkenyl- and aryl-substituted compounds, N,N-dibenzylcyclopropylamines can be debenzylated by catalytic hydrogenation to the primary cyclopropylamines as demonstrated for 10a and 10d to yield the fully deprotected 10c (93%) and mono-Boc-protected 10f (98%), respectively. The latter are interesting templates for combinatorial syntheses of libraries of small molecules with a well defined distance of 4.3 Angstrom between two nitrogen atoms. [References: 56]
机译：在四异丙醇钛或甲基三异丙醇钛以及各种环和无环烯烃与链二烯的存在下，用环己基溴化镁处理二苄基甲酰胺，得到新的单取代和双取代的以及双环的二烷基二烷基环丙胺（表1-3），收率范围从18 90％（大多数情况下约为55％）。 3-苄基-6-（N，N'-二苄氨基）-3-氮杂双环[3.1.0]己烷（10 a）和正交双保护的3-叔丁氧基羰基-6-（N，N-二苄基）-3-以特别高的收率（87、90和90）获得了氮杂双环[3.1.0]己烷（10d）以及类似的6-（N，N-二苄氨基）双环[3.1.0]己烷（12）作为纯的exo非对映异构体。 N-苄基吡咯啉（15a），N-Boc-吡咯啉（15d; Boc =叔丁氧羰基）和环戊烯（分别为88％）。 1,3-丁二烯（52）和取代的1,3-丁二烯也被氨基环丙烷化得很好，从而以良好的收率（51-64％）得到2-乙烯基环丙胺。除烯基和芳基取代的化合物外，N，N-二苄基环丙胺可通过催化氢化反应脱苄基成伯环丙胺，如10a和10d所示，得到完全脱保护的10c（93％）和单-Boc保护的10f（98） ％）， 分别。后者是用于小分子文库的组合合成的有趣模板，两个氮原子之间的明确定义的距离为4.3埃。 [参考：56]

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