121618-60-8Relevant articles and documents
Metallophthalocyanine complex, Cr(TBPC)OTf: An efficient, recyclable Lewis acid catalyst in the regio- and stereoselective rearrangement of epoxides to aldehydes
Suda, Kohji,Nakajima, Shin-Ichiro,Satoh, Yasumi,Takanami, Toshikatsu
, p. 1255 - 1257 (2009)
The metallophthalocyanine complex Cr(TBPC)OTf works as a highly efficient, recyclable Lewis acid catalyst for the regio- and stereoselective rearrangements of epoxides to aldehydes. The Royal Society of Chemistry.
Picolinoxy group, a new leaving group for anti SN2 selective allylic substitution with Aryl Anions Based on Grignard Reagents
Kiyotsuka, Yohei,Acharya, Hukum P.,Katayama, Yuji,Hyodo, Tomonori,Kobayashi, Yuichi
supporting information; experimental part, p. 1719 - 1722 (2009/04/10)
The picolinoxy group was found to be an extremely powerful leaving group for allylic substitution with aryl nucleophiles derived from ArMgBr and CuBr?Me2S. The substitution proceeds with anti SN2 pathway and with high chirality transfer. The electron-withdrawing effect of the pyridyl group and chelation to MgBr2 are likely the origin of success. Results suggesting these effects were obtained.
Organoaluminum-catalyzed rearrangement of epoxides a facile route to the synthesis of optically active β-siloxy aldehydes
Maruoka, Keiji,Ooi, Takashi,Nagahara, Shigeru,Yamamoto, Hisashi
, p. 6983 - 6998 (2007/10/02)
A new, stereocontrolled rearrangement of epoxy silyl ethers leading to β-siloxy aldehydes has been effected with stoichiometric use of exceptionally bulky, oxygenophilic methylaluminum bis(4-bromo-2,6-di-trert-butylphenoxide) (MABR) under mild conditions. Used in combination with the Sharpless asymmetric epoxidation of allylic alcohols, this rearrangement represents a new approach to the synthesis of various optically active β-hydroxy aldehydes, useful intermediates in natural product synthesis. The modified organoaluminum reagent, MABR is also applicable to the transformation of a variety of simple epoxides to carbonyl compounds with high efficiency and selectivity. Further, the catalytic version for the rearrangement of epoxy silyl ethers as well as simple epoxides has been newly devised. The scope and limitation of this catalytic method has been clarified with various epoxy substrates.