Asymmetric Vinylogous Aldol-type Reactions of Aldehydes with Allyl Phosphonate and Sulfone

被引：13
|
作者：
Yue, Wen-Jun [1 ]
Zhang, Cheng-Yuan [1 ]
Yin, Liang [1 ]
机构：
[1] Univ Chinese Acad Sci, Chinese Acad Sci, CAS Key Lab Synthet Chem Nat Subst, Ctr Excellence Mol Synth,Shanghai Inst Organ Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
来源：
ISCIENCE | 2019年 / 14卷
基金：
中国国家自然科学基金;
关键词：
Chemistry; Organic Synthesis; Stereochemistry;
D O I：
10.1016/j.isci.2019.03.010
中图分类号：
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号：
07 ; 0710 ; 09 ;
摘要：
Two catalytic asymmetric vinylogous aldol-type reactions of aldehydes with ally! phosphonate and allyl sulfone have been uncovered in good to high yields for the first time, The bulky ligand-(R)-DTBM-SEGPHOS-was found to be the key to perfectly control both regio- and enantioselectivities. Transformations of the vinylogous products (including Horner-Wadsworth-Emmons and Julia olefinations) were successfully realized by virtue of the phosphonate and sulfone moieties. Moreover, the present methodology was successfully applied in the asymmetric synthesis of natural products.
引用
收藏
页码：88 / +
页数：253
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