Acetates alkenes

D. Berger, L. E. Overman, and P. A. Renhowe, Total synthesis of (+)-isolaurepinnacin. Use of acetal-alkene cyclizations to prepare highly functionalized seven-membered cyclic ethers, J. Am. Chem. Soc., 119 (1997) 2446-2452. 

Berger D, Overman LE, Renhowe PA (1997) Total Synthesis of (+)-Isolaurepinnacin. Use of Acetal-Alkene Cyclizations to Prepare Highly Functionalized Seven-Membered Cyclic Ethers. J Am Chem Soc 119 2446... 

Fig. Synthesis of an alcohol from an alkene using mercuric acetate. Alkenes to Ethers...

Dehydrogenation reactions using sulfur reagents have been shown to tolerate a variety of other functional groups, including acetals, alkenes, epoxides and silyl ethers, - but the milder procedures available using selenenyl moieties may offer advantages in more sensitive molecules (see Section 2.2.4). 

Alkylations of boron-stabilized carbanions have been carried out with primary alkyl halides containing acetal, alkene, alkyne, chloride, cyano, ester and tosylate groups, though a ketone group was not tolerated. ... 

Acetal Alkene Temp (°C), Time (h) Cyclopropane Product ... 

Lactams can be prepared by [2 + 2] cycloadditions of mines and ketenes50- 52, iniines and ester enolatcs53, imines and silyl ketene acetals, alkenes and isocyanates54 56 and carbodi-imides and ketenes. The stereospecificity of these reactions has been extensively investigated due to the tremendous practical importance of 0-lactam antibiotics57 -59,1I3. 

Further problems arise with respect to the /V,0-ketene acetal alkene geometry with substrates unsymmetrically substituted at C-l resulting in a decrease in selectivity, e.g., 13642. 

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