105762-57-0Relevant articles and documents
Regioselective synthesis of substituted (3E)-1,3-dienes from chelated allyl-ironcarbene complexes and potassium enoxyborates
B?hmer, Jutta,Hampel, Frank,Schobert, Rainer
, p. 661 - 667 (1997)
The addition of potassium enoxyborates to the chelated allyl-ironcarbene complex 1 leads to the corresponding η-(3E)-1,3-diene complexes 2 in fair yields. Complexes 2 can be demetalated with ceric ammonium nitrate (CAN) to give unrearranged (3E)-6-oxo-1.3-dienes 3. Prior to decomplexation, the carbonyl group can be further modified. This is demonstrated by the syntheses of the natural terpene alcohol hotrienol and of a complexed methylene- separated dienyne. Potassium enoxyborates are superior to lithium enolates as they are readily prepared in situ from a variety of aldehydes and ketones which do not form sufficiently stable lithium derivatives. In contrast to lithium enolates, only C- C coupling products derived from the 'kinetic' regioisomers are formed from unsymmetrical aliphatic ketones.
Facile synthesis of silyl enol ethers by Mg-promoted coupling of aliphatic carbonyl compounds with trimethylsilyl chloride
Ishino, Yoshio,Kita, Yoshio,Maekawa, Hirofumi,Ohno, Toshinobu,Yamasaki, Yasuhiro,Miyata, Toshiyuki,Nishiguchi, Ikuzo
, p. 1349 - 1352 (2007/10/03)
Treatment of aliphatic carbonyl compounds with trimethylsilyl chloride with Mg turning for Grignard reaction without any pre-treatment in N,N- dimethylformamide at room temperature brought about highly facile, effective and stereoselective coupling to give the corresponding silyl enol ethers in good yields.
CHLOROSILANE-ACCELERATED CONJUGATE ADDITION OF CATALYTIC AND STOICHIOMETRIC ORGANOCOPPER REAGENTS
Matsuzawa, Satoshi,Horiguchi, Yoshiaki,Nakamura, Eiichi,Kuwajima, Isao
, p. 349 - 362 (2007/10/02)
Trialkylsilyl chlorides, particularly in combination with hexamethylphosphoramide or 4-dimethylaminopyridine, dramatically accelerates the conjugate addition of catalytic and stoichiometric organocopper reagents onto enones, enals, and enoates, in which very high degrees of stereo- and chemoselectivities were observed.
