کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
5218713 | 1383335 | 2012 | 6 صفحه PDF | دانلود رایگان |
عنوان انگلیسی مقاله ISI
Bis(oxazoline)-ligand-mediated asymmetric [2,3]-Wittig rearrangement of benzyl ethers: reaction mechanism based on the hydrogen/deuterium exchange effect
دانلود مقاله + سفارش ترجمه
دانلود مقاله ISI انگلیسی
رایگان برای ایرانیان
کلمات کلیدی
موضوعات مرتبط
مهندسی و علوم پایه
شیمی
شیمی آلی
پیش نمایش صفحه اول مقاله
چکیده انگلیسی
We have investigated the mechanism of chiral induction in the asymmetric [2,3]-Wittig rearrangement of allyl benzyl ether in the presence of a bis(oxazoline) chiral ligand [(S,S)-Box-tBu] by comparing the reaction of both enantiomers of monodeuterated benzyl ether 1a-d. As a result, we found that chirality was induced via enantioselective deprotonation followed by efficient chirality transfer of the resulting chiral benzyl carbanion with the inversion of stereochemistry. It was revealed that the chiral ligand facilitates selective deprotonation as well as prevents the chiral carbanion from racemization. Moreover, we examined the effect of the o-methoxy substituent on the benzene ring.
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron - Volume 68, Issue 22, 3 June 2012, Pages 4280-4285
Journal: Tetrahedron - Volume 68, Issue 22, 3 June 2012, Pages 4280-4285
نویسندگان
Maria Kitamura, Yoshimi Hirokawa, Yuki Yoshioka, Naoyoshi Maezaki,