Tetrahedron p. 6983 - 6998 (1991)
Update date:2022-08-02
Topics:
Maruoka, Keiji
Ooi, Takashi
Nagahara, Shigeru
Yamamoto, Hisashi
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.
View MoreContact:
Address:308# dongwu avenue dongxihu district wuhan city
website:http://www.shengmaochem.com
Contact:86-27-82853423, 82819281
Address:Rm 202, A Unit Huaqiao Building No. 2, Lihuangpi Road, Wuhan, China
QINGDAO NEW FLOURISH INTERNATIOANAL TRADE CO., LTD.
Contact:+86 532 80861829
Address:No. 1, Yinchuan East Road, 266061, Qingdao, China
Nanjing Qirui Material Co., Ltd.
Contact:+86-25-52320053
Address:F4-5, #17 Building, Chuang Yi Yuan, No.6 Guanghua East Street, Nanjing, 210007 P.R.China
Chengdu King-tiger Pharm-chem. Tech. Co., Ltd
Contact:028-85317716
Address:Tianfu Life Science Park, No. 88 South Keyuan Road, Gaoxin District, Chengdu City, Sichuan Province, PRC.
Doi:10.1007/s10631-005-0032-3
(2005)Doi:10.1016/S0277-5387(00)83855-3
(1989)Doi:10.1021/acs.orglett.6b02321
(2016)Doi:10.1016/S0040-4039(00)80372-X
(1988)Doi:10.1002/adsc.200900548
(2009)Doi:10.1016/j.jfluchem.2009.11.005
(2010)