138436-32-5Relevant academic research and scientific papers
Asymmetric synthesis of protected α-alkyl-β-amino-δ-hydroxy esters by stereocontrolled elaboration of THYM*
Guanti, Giuseppe,Moro, Alberto,Narisano, Enrica
, p. 3203 - 3207 (2000)
Highly diastereoselective internal Michael addition of the carbamate moiety of enoate 1b [derived from asymmetrized tris(hydroxymethyl)methane (THYM*)] leads to oxazinone 4, which can, in turn, be alkylated with moderate to good diastereoselectivity in th
Stereodivergent synthesis of cis epoxides derived from asymmetrized 2-alkenyl-1,3-propanediols
Guanti, Giuseppe,Banfi, Luca,Merlo, Valeria,Narisano, Enrica,Thea, Sergio
, p. 9501 - 9516 (2007/10/02)
Cis epoxides of any desired absolute stereochemistry have been obtained in a high enantio- and diastereodivergent manner via diastereospecific epoxidation of asymmetrized (Z)-2-alkenyl-1,3-propanediols, in turn obtained through a chemoenzymatic route, and a protection-deprotection 'trick' on hydroxy groups.
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.
Protecting group controlled diastereoselective allylation of asymmetrized bis (hydroxymethyl) acetaldehydes (BHYMA)
Guanti, Giuseppe,Banfi, Luca,Narisano, Enrica
, p. 6939 - 6942 (2007/10/02)
MgBr2 catalysed allylation of a series of diprotected asymmetrized bis (Hydroxymethyl) acetaldehydes 2 with allyltributylstannane proceeds with good diastereoselectivity. The stereochemical results are in line with a cyclic chelated transition state, where only one of the two CH2OR appendages, due to the different nature of protecting groups, is capable of coordinating the Lewis acid.
