REACTIONS OF 6-[BIS(TRIMETHYLSILYL)AMINO]-5,6-DIHYDRO-4H-1,2-OXAZINES

被引：0

作者：

PAULINI, K

GEROLD, A

REISSIG, HU

机构：

[1] TH DARMSTADT,INST ORGAN CHEM,D-64287 DARMSTADT,GERMANY

[2] TECH UNIV DRESDEN,INST ORGAN CHEM,D-01062 DRESDEN,GERMANY

来源：

LIEBIGS ANNALEN | 1995年 / 04期

关键词：

1,2-OXAZINES, BIS(TRIMETHYLSILYL)AMINO-SUBSTITUTED; HYDROGENOLYSIS; DEPROTONATION; ALKYLATION; DEUTERATION;

D O I：

暂无

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

1,2-Oxazine 1 ws converted into an unusual condensation product 5 by treatment with tetra-n-butylammonium fluoride. the hydrogenolysis of 1 with Pd/C as catalyst provided the expected primary amine 9, whereas the same reaction with the ethoxycarbonyl-substituted 1,2-oxazine 2 as starting material gave the 4-methylproline derivative 10 after N-protection. Deprotonation at C-4 of 1 required rather harsh conditions but cleanly afforded the corresponding lithiated intermediate 11. Treatment of 11 with electrophiles provided the C-4-substituted derivatives 12-16 in good to moderate yield, but generally with very high diastereoselectivity. The overall substitution process preferentially occurs with retention of configuration which is explained by assuming ion pair structure B for intermediate 11.

引用

页码：667 / 671

页数：5

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