Ketone From alkene

Most important for the synthetic chemist is an index to the synthesis of functional groups, e.g. synthesis of alkenes from ketones, as well as conversion of ketones to alkenes. 

Black. T.H. Zhang, Y. Huang, J. Smith, D.C. Yates, B.E. Synth. Commun., 1995, 25, 15 Related Methods Section 207 (Alkenes from Ketones). 

The original Shapiro reaction involves the preparation of unfiinctionalized alkenes from ketone tosyl-hydrazones by quenching of the in situ generated alkenyllithium reagents with water. Recent applications of this reaction in natural product synthesis include the synthesis of 9(0)-methanoprostacyclin (Scheme 12), the in vitro conversion of humulene to A ( -capnellene (Scheme 13), the synthesis of die basic skeleton of isoadsirene (equation S2) ° and the total synthesis of the eudesmanolides rothin A and rothin B (equation 53). ... 

Table 11. 1-[l-(Trimethylsilyl)cyclopropyl]alkenes from Ketones and a-Bromovinyltrimethylsilane (Method A) or l-Bromo-l-(trimethylsilyl)cyclopropene (Method B) ... 

Related Methods Section 207 (Alkenes from Ketones). 

Examples of name reactions may be found by first considering the nature of the starting material and product. The Wittig reaction, for instance, is given in Section 199 (Alkenes from Aldehydes) and in Section 207 (Alkenes from Ketones). The aldol condensation may be found in the chapters on difunctional compounds in Section 324 (Alcohol, Thiol-Aldehyde) and in Section 330 (Alcohol, Thiol-Ketone). Examples of the synthetically important alkene metathesis reaction are provided primarily in Section 209 (Alkenes from Alkenes). 

The hydroboration of enamine is remarkable regio- and chemoselective as the boron adds to the electron-rich enamine double bond. Consequently, hydroboration of enamines and the treatment of the resulting trialkylboranes with methanol afford the corresponding alkenes in excellent yield [13]. The process is a general procedure for the synthesis of terminal alkenes from aldehydes and internal or cyclic alkenes from ketones (Eq. 24.5). 

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