The first asymmetric ring-expansion carbonylation of meso-epoxides.
نویسندگان
چکیده
The first asymmetric ring-expansion carbonylation of meso-epoxides to β-lactones is reported. Two structurally diverse chiral Cr(III) chloro complexes in conjunction with Co(2)(CO)(8) were shown to be competent catalytic systems for this transformation, displaying significant levels of asymmetric induction of up to 56% ee.
منابع مشابه
Carbonylation of heterocycles by homogeneous catalysts.
This article summarizes the recent developments (particularly the uses of homogeneous organometallic catalysts) in ring-opening carbonylations, ring-opening carbonylative polymerizations and ring-expansion carbonylations of heterocycles such as epoxides, aziridines, lactones and oxazolines.
متن کاملHeterogeneous Epoxide Carbonylation by Cooperative Ion-Pair Catalysis in Co(CO)4–-Incorporated Cr-MIL-101
Despite the commercial desirability of epoxide carbonylation to β-lactones, the reliance of this process on homogeneous catalysts makes its industrial application challenging. Here we report the preparation and use of a Co(CO)4--incorporated Cr-MIL-101 (Co(CO)4⊂Cr-MIL-101, Cr-MIL-101 = Cr3O(BDC)3F, H2BDC = 1,4-benzenedicarboxylic acid) heterogeneous catalyst for the ring-expansion carbonylation...
متن کاملA covalent triazine framework-based heterogenized Al–Co bimetallic catalyst for the ring-expansion carbonylation of epoxide to β-lactone
b-Lactones are important intermediates for ring-opening polymerization to form poly(b-hydroxyalkanoates), a naturally occurring biodegradable and thermoplastic polyester. Many synthetic methods are available for preparing b-lactones, among which catalytic ring-opening carbonylation of epoxides has received considerable attention because of its ability to produce enantiopure b-lactones. Over the...
متن کاملAllenes in asymmetric catalysis: asymmetric ring opening of meso-epoxides catalyzed by allene-containing phosphine oxides.
Unsymmetrically substituted allenes (1,2-dienes) are inherently chiral and can be prepared in optically pure form. Nonetheless, to date the allene framework has not been incorporated into ligands for asymmetric catalysis. Since allenes project functionality differently than either tetrahedral carbon or chiral biaryls, they may create complementary chiral environments. This study demonstrates th...
متن کاملB-podands as efficient catalysts for the ring opening of epoxides in water: A versatile and atom economical method for the synthesis of vicinal azidoalcohols
For the first time B-podands have been studied as an efficient and powerful catalysts in the ring opening of epoxides with azide anion in water. The reaction afforded the corresponding 1,2-azidoalcohols with high regioselectivity under mild reaction conditions and in a highly atom economic fashion.
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Chemical communications
دوره 48 81 شماره
صفحات -
تاریخ انتشار 2012