Borane and alane reductions of bulky N,N′-diaryl-1,3-diimines:: structural characterization of products and intermediates in the diastereoselective synthesis of 1,3-diamines

被引：19

作者：

Carey, DT ^{[1
]}

Mair, FS ^{[1
]}

Pritchard, RG ^{[1
]}

Warren, JE ^{[1
]}

Woods, RJ ^{[1
]}

机构：

[1] UMIST, Dept Chem, Manchester M60 1QD, Lancs, England

来源：

DALTON TRANSACTIONS | 2003年 / 19期

关键词：

D O I：

10.1039/b306401h

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Two new C-2-symmetric diazaborinanes were prepared by diastereoselective intramolecular dihydroboration of bulky 1,3-diamines, the remarkably stable l-[HB(2,6-Pr-2(i)-C6H3NCHMe)(2)CMe2], from which it was not possible to isolate free diimine, and the less bulky l-[HB(2-Pr-i-C6H4NCHMe)(2)CMe2], which yielded l-(2-Pr-i-C6H4NHCHMe)(2)CMe2 on acid work up. The BH3 reductions were highly diastereoselective for l-products (de > 95%). Use of AlCl3/LiAlH4 mixtures in diethyl ether gave lower (de approximate to 75%) and opposite selectivity, yielding predominantly u-(2,6-Pr-2(i)-C6H3NHCHMe)(2)CMe2 upon work up, via au-[H2Al(2,6-Pr-2(i)-C6H3)NHCHMeCMe2CHMeN(2,6-Pr-2(i)-C6H3)] intermediate in a two-step reduction. All products were characterized crystallographically.

引用

页码：3792 / 3798

页数：7

共 23 条

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