1,2-amino alcohols by photocycloaddition ring opening sequences

被引：0

作者：

Schroder, J ^{[1
]}

Bach, T ^{[1
]}

机构：

[1] Univ Marburg, Fachbereich Chem, D-35032 Marburg, Germany

来源：

JOURNAL OF INFORMATION RECORDING | 1998年 / 24卷 / 3-4期

关键词：

1,2-amino alcohols; oxetanes; photochemistry; natural products;

D O I：

暂无

中图分类号：

T [工业技术];

学科分类号：

08 ;

摘要：

The Paterno-Buchi reaction of aldehydes and N-acyl enamines generate cis-3-aminooxetanes with high regio- and satisfactory diastereoselectivities (d.r.9/1). Different ring opening reaction opens routes to syn- and anti-1, 2-amino alcohols like pseudoephedrine (10) and ephedrine (13). Another natural product containing a cis-3-aminooxetane structure is oxetin (14), an antibiotic beta-amino acid. It was prepared by photocycloaddition and removal of protecting groups.

引用

页码：285 / 288

页数：4

共 50 条

[1] Practical synthesis of enantiopure cyclic 1,2-amino alcohols via catalytic asymmetric ring opening of meso epoxides
Schaus, SE
Larrow, JF
Jacobsen, EN
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (12): : 4197 - 4199
[2] General and facile synthesis of 1,2-amino alcohols
Jung, DY
Ko, CH
Kim, YH
SYNLETT, 2004, (07) : 1315 - 1317
[3] Metal-free synthesis of 1,2-amino alcohols by one-pot olefin aziridination and acid ring-opening
Hua, Yong-Gang
Yang, Qian-Qian
Yang, Yi
Wang, Mei-Jing
Chu, Wen-Chao
Bai, Peng-Yan
Cui, De-Yun
Zhang, En
Liu, Hong-Min
TETRAHEDRON LETTERS, 2018, 59 (28) : 2748 - 2751
[4] Highly Regio- and Stereodivergent Access to 1,2-Amino Alcohols or 1,4-Fluoro Alcohols by NHC-Catalyzed Ring Opening of Epoxy enals
Poh, Si Bei
Ong, Jun-Yang
Lu, Shenci
Zhao, Yu
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (06) : 1645 - 1649
[5] Photocycloaddition of N-acyl enamines to aldehydes and its application to the synthesis of diastereomerically pure 1,2-amino alcohols
Bach, T
Schröder, J
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (04): : 1265 - 1273
[6] ZnCl2 Catalyzed Ring-Opening Reaction of Symmetrical Epoxides with Aromatic Amines for the Synthesis of 1,2-Amino Alcohols
Zhou, Xiao-Yu
Chen, Xia
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2022, 54 (01) : 56 - 64
[7] A chiral ketone for enantioselective recognition of 1,2-amino alcohols
Nandhakumar, Raju
Guo, Yong-En
Park, Hytinjung
Tang, Lijun
Nam, Wonwoo
Kim, Kwan Mook
TETRAHEDRON LETTERS, 2007, 48 (37) : 6582 - 6585
[8] A novel and efficient oxidation of 1,2-amino alcohols to dialkylamides
García-Valverde, M
Pedrosa, R
Vicente, M
SYNLETT, 2002, (12) : 2092 - 2094
[9] Stereoselective synthesis of enantioenriched acetylenic 1,2-amino alcohols
Chemla, Fabrice
Ferreira, Franck
Gaucher, Xavier
Palais, Laetitia
SYNTHESIS-STUTTGART, 2007, (08): : 1235 - 1241
[10] EFFICIENT PREPARATION OF BIOLOGICALLY IMPORTANT 1,2-AMINO ALCOHOLS
Gupta, Pankaj
Rouf, Abdul
Shah, Bhahwal A.
Mukherjee, Debaraj
Taneja, Subhash C.
SYNTHETIC COMMUNICATIONS, 2013, 43 (04) : 505 - 519

← 1 2 3 4 5 →