Bulletin of the Chemical Society of Japan p. 231 - 235 (2000)
Update date:2022-08-02
Topics:
Nakamura, Hiroyuki
Fujiwara, Masaru
Yamamoto, Yoshinori
Enantiomerically pure L-BPA (4-borono-L-phenylalanine) was synthesized from L-tyrosine or 4-iodo-L-phenylalanine derivatives using the palladium- catalyzed cross-coupling reaction of pinacolborane (2,3-dimethyl-2,3- butanediolatoboron). Cbz-Tyr(Nf)-OBzl (2b) underwent the cross-coupling reaction with pinacolborane (1) in the presence of [PdCl2(PPh3)2] catalyst to give N-benzyloxycarbonyl-4-(2,3-dimethyl-2,3-butanediolatoboryl)-L- phenylalanine benzyl ester (3a) in 58% yield. The reaction of the 4-iodo-L- phenylalanine derivatives, such as N-benzyloxycarbonyl-4-iodo-L-phenylalanine benzyl ester (2c), N,N-dibenzyl-4-iodo-L-phenylalanine benzyl ester (2d), (4S)-3-benzyloxycarbonyl-4-(4-iodobenzyl)-5-oxazolidinone (2e), and (4S)-3-t- butyloxycarbonyl-4-(4-iodobenzyl)-5-oxazolidinone (2f), with 1 proceeded very smoothly in the presence of [PdCl2(dppf)] catalyst, giving N- benzyloxycarbonyl-4-(2,3-dimethyl-2,3-butanediolatoboryl)-L-phenylalanine benzyl ester (3a), N,N-dibenzyl-4-(2,3-dimethyl-2,3-butanediolatoboryl)-L- phenylalanine benzyl ester (3b), (4S)-3-benzyloxycarbonyl-4-[4-(2,3-dimethyl- 2,3-butanediolatoboryl)benzyl]-5-oxazolidinone (3c), and (4S)-3- butyloxycarbonyl-4-[4(2,3-dimethyl-2,3-butanediolatoboryl)benzyl]-5- oxazolidinone (3d), respectively, in high yields. Deprotection of 3a-d gave enantiomerically pure L-BPA in high total yields.
View MoreBeijing Mashi Fine Chemical Co.,Ltd.
Contact:+86-10-61271592
Address:Room 506, Section B, Kaichi Mansion, Industrial Development
Contact:86-512-87182056
Address:No.128 Fangzhou Rd, Suzhou Industrial Park, China, 215125, China
KINHENG CHEMICAL(SHANGHAI)CO., LTD.
Contact:+8621-60490170
Address:Room401, No.28,Lane 189, Yangshupu Rd. Shanghai, China.
TIANJIN GST CHEMICAL TECHNOLOGY CO., LTD
Contact:+86-22-25210964
Address:Room. 208, No. -12-C, No. 13, Xinbei Road, Tanggu District, New Haixin Area, Tianjin City, China
Contact:+8618766299236
Address:ROOM808, BUILDING2,NO.230 SHEN ZHEN ROAD, LAOSHAN DISTRICT
Doi:10.1007/BF00571211
()Doi:10.1021/ja01556a016
(1958)Doi:10.1002/ejoc.200701010
(2008)Doi:10.1016/0022-328X(94)80033-2
(1994)Doi:10.1021/jo00412a022
(1978)Doi:10.1021/jo01340a027
(1966)