TY - JOUR
T1 - Understanding the reactivity of acyl anion equivalents: the epoxide ring opening case
AU - Eger, W.
AU - Grange, R.
AU - Schill, H.
AU - Goumont, R.
AU - Clark, Tim
AU - Williams, C.
PY - 2011/5
Y1 - 2011/5
N2 - Acyl anion equivalents (umpolung) are the practitioner's first choice en route to 1,3-hydroxy keto compounds from epoxides. Why? This investigation evaluates computationally and experimentally the reactivity of a near comprehensive range of acyl anion equivalents using epoxide ring opening as a test vehicle. Reactivity understanding, reactivity order, surprise failures in performance, along with unprecedented, but far from superior, reactivity of TosMIC is presented for the first time.
AB - Acyl anion equivalents (umpolung) are the practitioner's first choice en route to 1,3-hydroxy keto compounds from epoxides. Why? This investigation evaluates computationally and experimentally the reactivity of a near comprehensive range of acyl anion equivalents using epoxide ring opening as a test vehicle. Reactivity understanding, reactivity order, surprise failures in performance, along with unprecedented, but far from superior, reactivity of TosMIC is presented for the first time.
U2 - 10.1002/ejoc.201001680
DO - 10.1002/ejoc.201001680
M3 - Article
VL - 2011
SP - 2548
EP - 2553
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
SN - 1434-193X
IS - 3
ER -