Stereoselective synthesis of di- and monofluoromethylated vicinal ethylenediamines with di- and monofluoromethyl sulfones.
Stereoselective synthesis of di- and monofluoromethylated vicinal ethylenediamines with di- and monofluoromethyl sulfones.
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DOI：
10.1021/jo070094w
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发表时间：
2007-03
期刊：
影响因子：
--
通讯作者：
Jun Liu;Ya Li;Jinbo Hu
中科院分区：
文献类型：
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作者：
Jun Liu;Ya Li;Jinbo Hu
用PhSO_2CF_2 H和PhSO_2CH_2F试剂对α-氨基N-叔丁基亚磺酰亚胺（3）进行非对映选择性亲核（苯磺酰基）二氟甲基化和（苯磺酰基）单氟甲基化反应，高产率（73-99%）和优良的非对映选择性（dr>99：1）得到产物4或5。化合物4和5经还原性二甲酰化和酸催化醇解后，可以很容易地转化为手性α-二氟甲基化或α-单氟甲基化乙二胺，产率较高。
The diastereoselective nucleophilic (phenylsulfonyl)difluoromethylation and (phenylsulfonyl)monofluoromethylation of alpha-amino N-tert-butanesulfinimines (3) by using PhSO2CF2H and PhSO2CH2F reagents gave products 4 or 5 in high yields (73-99%) and with excellent diastereoselectivity (dr up to >99:1). After subsequent reductive desulfonylation and acid-catalyzed alcoholysis, compounds 4 and 5 could be readily transformed to chiral alpha-difluoromethylated or alpha-monofluoromethylated ethylenediamines in good yields.