Enantioselective synthesis of α-sulfenylated ketones and aldehydes via α-thiolation of metalated SAMP/RAMP hydrazones
Enantioselective synthesis of α-sulfenylated ketones and aldehydes via α-thiolation of metalated SAMP/RAMP hydrazones
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DOI:
10.1016/s0040-4020(98)00481-5
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发表时间:
1998-08-27
期刊:
影响因子:
2.1
通讯作者:
Mies, W
中科院分区:
文献类型:
--
作者:
Enders, D;Schäfer, T;Mies, W
Asymmetric cc-sulfenylation of lithiated SAMP/RAMP hydrazones (S)-2 with disulfides afforded alpha-thiolated hydrazones (S,R)-3 in good yields (48-87%) and high diastereomeric excesses (91-96%). Subsequent oxidative cleavage or acidic hydrolysis of the hydrazones furnished alpha-Dthiolated ketones (R)-4a-d with high enantiomeric excesses (87->96%). alpha-Sulfenylated aldehydes (R)-8a-d were prepared by a similar reaction sequence with 45-93% ee. (C) 1998 Elsevier Science Ltd. All rights reserved.