ChemInform Abstract: Regio- and Enantioselective Synthesis of α-Silyl Aldehydes and Ketones via SAMP/RAMP Hydrazones.
✍ Scribed by D. ENDERS; B. B. LOHRAY; F. BURKAMP; V. BHUSHAN; R. HETT
- Book ID
- 112037402
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 38 KB
- Volume
- 27
- Category
- Article
- ISSN
- 0931-7597
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Asymmetric ot-sulfenylation of lithiated SAMP/RAMP hydrazoncs (3")-2 with disulfides afforded tz-thiolated hydrazones (S,R)-3 in good yields (48-87%) and high diastcreomeric excesses (91-96%). Subsequent oxidative cleavage or acidic hydrolysis of the hydrazones furnished a-thiolated ketones (R)-4a.d
A new versatile and efficient regio-, diastereo-, and enantioselective synthesis of vicinal diols s-trans-4, s-trans-5, and s-cis-4 is described. Symmetrical ketones are converted into their SAMP-or RAMP-hydrazones which are then silylated with (isopropy1oxy)dimethylsilyl chloride, followed by ozono
## Abstract Asymmetric Michael addition of lithiated methyl ketone SAMP hydrazones (S)‐3 to a variety of alkenylphosphonates (E)‐2 followed by oxidative cleavage of the 1,4‐adducts (__S,S__)‐4 by ozonolysis afforded 2‐substituted 4‐oxophosphonates (__S__)‐5 in usually moderate to very good overall