Bulletin of the Chemical Society of Japan p. 237 - 242 (2000)
Update date:2022-08-04
Topics:
Senda
Kikuchi
Inui
Itoh
A directive effect of the 2-axial hydroxy group appeared in the LiAlH4, NaBH4, and Zn(BH4)2 reduction of cyclohexanone, while the 3-axial hydroxy group exhibited a steric hindrance. The distance between the carbonyl carbon and the hydroxy group interacting with the hydride reagent was responsible for such a difference. In the reduction of Na[B(OAc)3H], the 2- and 3-axial hydroxycyclohexanones gave the products obtained by the hydride approaching from the side of the hydroxy group. The key point of the stereoselectivity was the formation of Na[B(OAc)2(OR)H, which was more reactive than the parent hydride, by exchanging the acetate ion with the alkoxide. Although the reduction was performed under the condition that the hydride/substrate ratio was 1, the conversion of the hydroxy ketone to an alcohol were < 50% for the LiAlH4, NaBH4, and Zn(BH4)2 reductions in tetrahydrofuran. The conversions in the NaBH4 reduction in ethanol were > 90%.
View MoreContact:+8613400661290
Address:No 908,Kangwan Rd, Liuyang Economic
QINGDAO TAOSIGN INTERNATIONAL TRADE CO.,LIMITED
Contact:+86-0532-82683616
Address:RM1402, Doublestar Seacoase 7#, No. 5 Guizhou Road, Qingdao, Shandong, China
JIANGXI AIFEIMU TECHNOLOGY CO.,LTD
Contact:+86-570-6040289
Address:FINECHEMICAL PARK,ZIBU TOWN,WANNIAN COUNTY,JIANGXI PROV.,CHINA,ZIP
SICHUAN ZHONGBANG NEW MATERIAL CO., LTD
website:http://www.zhongbangst.com
Contact:86-830-2585019
Address:sichuan,china
Contact:0027-717-456976
Address:2ND FLOOR, 325 VAUSE ROAD, OVERPORT, 4001, SOUTH AFRICA
Doi:10.2174/157017812803521199
(2012)Doi:10.1039/b713888a
(2008)Doi:10.1055/s-2007-990867
(2007)Doi:10.1002/hlca.19590420225
(1959)Doi:10.1021/jo702409y
(2008)Doi:10.1021/acs.joc.7b00567
(2017)