Stereoselective synthesis of functionalized allenes from tartaric acid

被引：3
|
作者：
Shruthi, Kodambahalli S. [1 ]
Singh, Piyal [1 ]
Prasad, Kavirayani R. [1 ]
机构：
[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India
来源：
TETRAHEDRON | 2020年 / 76卷 / 50期
关键词：
Chiral allenes; Claisen rearrangement; Stereoselective reduction; Chiral pool; ENANTIOSPECIFIC SYNTHESIS; CLAISEN REARRANGEMENT;
D O I：
10.1016/j.tet.2020.131706
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Desymmetrization of the C-2-symmetric bis-dimethylamide derived from tartaric acid by controlled addition of alkynyl lithium reagents furnished the mono alkynyl ketones which on reduction produced the corresponding propargyl alcohols with good diastereoselectivity. The propargyl alcohols were transformed to allenes using Claisen rearrangement. The formed allenes serve as a precursor for the synthesis of one of the THP units of the natural product sorangicin and for the synthesis of the polyhydroxy unit present in natural product anamarine. (C) 2020 Elsevier Ltd. All rights reserved.
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页数：11
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