133377-92-1Relevant academic research and scientific papers
Chemoenzymatic Preparation of Asymmetrized Tris(hydroxymethyl)methane (THYM*) and of Asymmetrized Bis(hydroxymethyl)acetaldehyde (BHYMA*) as New Highly Versatile Chiral Building Blocks
Guanti, Giuseppe,Banfi, Luca,Narisano, Enrica
, p. 1540 - 1554 (2007/10/02)
A series of asymmetrized tris(hydroxymethyl)methanes 2 and bis(hydroxymethyl)acetaldehydes 3 have been prepared in both enantiomeric forms through a chemoenzymatic methodology.The key step is the highly enantioselective PPL-catalyzed monohydrolysis of 2(E)-alkenyl-1,3-diacetoxypropanes 25-27.A careful study on the effect of unsaturations adjacent to the prochiral center in a series of 2-substituted 1,3-diacetoxypropanes has confirmed the suggested beneficial effect of a ? system in that position but has also unveiled an unprecedented dramatic effect of double-bond configuration on enantioselectivity.A new empirical model for the interpretation of these and other results, based both on polarity and steric arguments, is proposed.This study provides a general protocol for the efficient synthesis of asymmetrized 1,3-propanediols bearing in position 2 saturated or unsaturated carbon chains.
Enzymes in Organic Synthesis: Remarkable Influence of a ? System on the Enantioselectivity in PPL Catalysed Monohydrolysis of 2-Substituted 1,3-Diacetoxypropanes.
Guanti, Giuseppe,Banfi, Luca,Narisano, Enrica
, p. 721 - 724 (2007/10/02)
The results of PPL catalysed monohydrolysis of a series of 2-substituted-1,3-diacetoxypropanes showed that alkinyl and (E) alkenyl substituents led to improvement of yield and enantioselectivity, compared to their saturated analogues.On the contrary, (Z) alkenyl substituents provoked a net reversal of asymmetric induction.
ASYMMETRIZED TRIS (HYDROXYMETHYL)METHANE AS A HIGHLY STEREODIVERGENT CHIRAL BUILDING BLOCK: PREPARATION OF ALL FOUR STEREOISOMERS OF PROTECTED 2-HYDROXYMETHYL-1,3-BUTANEDIOL
Guanti, Giuseppe,Banfi, Luca,Narisano, Enrica
, p. 6421 - 6424 (2007/10/02)
Monoacetate 3 is a synthetic equivalent of asymmetrized tris(hydroxymethyl)methane 1, which is a new chiral building block endowed with latent C3v symmetry.Thanks to this property, starting from a single enantiomer 3, it is possible to get not only both (R) and (S) aldehydes 7, but also all the stereoisomers deriving from addition of a C-nucleophile to 7, just relying on a single diastereocontrol (double stereodivergency).
