Journal of Organic Chemistry p. 4214 - 4223 (1984)
Update date:2022-09-26
Topics:
Heathcock, Clayton H.
Kiyooka, Syun-ichi
Blumenkopf, Todd A.
The Lewis acid mediated reactions of chiral aldehydes 1-4 and enones 5-8 with allylsilanes 9 and 10 have been investigated.With aldehyde 1 and enones 5-7, modest diastereofacial preferences are seen, in the sense predicted by application of Felkin's model for asymmetric induction.Aldehydes 2-4 and enone 8 appear to react by way of chelated intermediates.With these four compounds, the diastereofacial preferences are rather large and are in the sense that is consistend with attack of the allylsilane on the least hindered face of the chelated intermediate.In the reaction of the trans and cis enones 6 and 8 with allyltrimethylsilane, a dramatic reversal of diastereofacial preference is observed; enone 6 gives a 84:14 ratio of products, while enone 8 provides a 10:90 mixture of the same products.
View MoreContact:86-0574-87406360
Address:Haishu, Jishi'gang Village Jishi core Valley 1 Building 301 Room
Changzhou Anyi Biochem Co., Ltd.(expird)
Contact:+86-519-88836158
Address:no,51 caoda
zhangjiagang bonded areas banggao co;ltd
website:http://www.shunchangchem.com
Contact:0086-13921972933
Address:Dongsha Chemical Zone.Zhangjiagang, Jiangsu Province
BrightGene Bio-Medical Technology Co., Ltd.
website:https://en.bright-gene.com/
Contact:+86-512-62551801
Address:Building C25 - C31, No. 218 Xinghu Road, Suzhou Industrial Park, Suzhou, Jiangsu, China.
Skyrun Industrial Co.,Ltd(expird)
website:http://www.chinaskyrun.com
Contact:0086-576-84610586
Address:Chemical Development Zone
Doi:10.1021/jo00176a007
(1984)Doi:10.1016/S0040-4039(00)99206-2
(1989)Doi:10.1021/ja057389g
(2006)Doi:10.1055/s-2005-922752
(2005)Doi:10.1021/np050403i
(2006)Doi:10.1016/S0040-4039(00)88311-2
(1983)