Tetrahydro-1,4-azaborines were accessed by hydroboration of N,N-diprenyltoluenesulfonamide 4. Conversion to the methylborinates 11 and 12 followed by heating with l-alanine and crystallization afforded (R,R,S)-13 (27%). Reduction of borinic acid (R,R)-18 with Soderquist’s KH* gave (R,R)-19, and hydride abstraction by TMSCl in the presence of alkenes resulted in hydroboration, 84–86% ee for (Z)-alkenes, but (E)-alkenes or 1,1-disubstituted alkenes gave <5% ee.

中文翻译：

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非外消旋C ₂对称四氢-1,4-氮杂萘胺的合成及硼氢化对映选择性的评价

N，N-二甲苯基甲苯磺酰胺4的硼氢化可得到四氢-1,4-氮杂萘。转化为甲基硼酸酯11和12，然后用1-丙氨酸加热并结晶，得到（R，R，S）-13（27％）。用Soderquist的KH *还原硼酸（R，R）-18可得到（R，R）-19，在烯烃存在下TMSCl提取氢化物可导致硼氢化，（Z的ee为84–86％）-烯烃，但（E）-烯烃或1,1-二取代的烯烃给出<5％ee。