Asymmetric synthesis of anti- and syn-2,3-diamino esters using sulfinimines. Water and concentration effects

利用亚磺酰亚胺不对称合成反式和顺式2,3-二氨基酯。水和浓度的影响

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Abstract

[reaction: see text] In the absence of water, an excess of the lithium enolate of N-(diphenylmethylene)glycine ethyl ester (4) adds to sulfinimines to give syn-2,3-diamino esters 6, and in the presence of water, this enolate gives the anti-2,3-diamino esters 5. These unusual results are interpreted in terms of those factors that inhibit the retro-Mannich fragmentation in the diamino esters.

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