Catalytic asymmetric [2,3]-sigmatropic rearrangement of sulfur ylides generated from copper(I) carbenoids and allyl sulfides.
نویسندگان
چکیده
Catalytic asymmetric sulfur ylide [2,3]-sigmatropic rearrangement of carbenoids generated from aryldiazoacetates has been investigated with a number of chiral Rh(II) and Cu(I) catalysts, and moderately high enantioselectivity (52-78% ee) can be achieved with Cu(MeCN)(4)PF(6)/2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline].
منابع مشابه
Catalytic asymmetric [2,3] sigmatropic rearrangement of sulfur ylides generated from carbenoids and propargyl sulfides
Catalytic asymmetric [2,3] sigmatropic rearrangement of sulfur ylides generated from aryldiazoacetates and propargyl sulfides with a number of chiral Rh(II) and Cu(I) catalysts have been investigated and moderately high enantioselectivities (up to 81% ee) have been achieved. © 2003 Elsevier Science Ltd. All rights reserved.
متن کاملHighly stereoselective [2,3]-sigmatropic rearrangement of sulfur ylide generated through Cu(I) carbene and sulfides.
A highly stereoselective [2,3]-sigmatropic rearrangement of sulfur ylide generated through Cu(I) carbene and allyl and propargyl sulfides by a double asymmetric induction approach that combines a chiral camphor sultam auxiliary and Cu(I) catalyst with chiral or achiral diimine ligands has been developed.
متن کاملHighly efficient [2,3]-sigmatropic rearrangement of sulfur ylide derived from Rh(II) carbene and sulfides in water
Introduction Since their discovery in the late 1960s, the [2,3]-sigmatropic rearrangements of sulfonium ylides have received considerable attention because of their applications in organic synthesis and their probable involvement in biochemical processes. The most common method for sulfonium ylide generation involves the removal of a proton from a sulfonium salt with a strong base. However, a m...
متن کاملA gold-catalysed fully intermolecular oxidation and sulfur-ylide formation sequence on ynamides.
An efficient C-O, C-S and C-C bond-forming sequence leads to functionalised compounds bearing sulfur-substituted quaternary carbons. Ynamides are employed as diazo-equivalents to access the [2,3]-sigmatropic rearrangements of allyl sulfonium ylides by a three-component chemoselective oxidation and intermolecular ylide formation.
متن کاملAsymmetric [2,3]-sigmatropic rearrangement of allylic ammonium ylides.
An asymmetric Lewis acid-mediated [2,3]-sigmatropic rearrangement of allylic amines has been developed, affording the corresponding homoallylic amines in good yield and excellent enantioselectivities. The rearrangement proceeds by complexation of the chiral Lewis acid to the amine followed by deprotonation and rearrangement.
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:
- The Journal of organic chemistry
دوره 67 16 شماره
صفحات -
تاریخ انتشار 2002