98168-21-9Relevant academic research and scientific papers
Enantioselective synthesis of allylic alcohols via an oxazaborolidinium ion catalyzed diels-alder/retro-diels-alder sequence
Jones, Simon,Valette, Damien
supporting information; experimental part, p. 5358 - 5361 (2010/01/19)
A triflimide-activated oxazaborolidine catalyst successfully promoted the asymmetric Diels-Alder reaction of 9-methylanthracene with methacrolein in high regio- and enantioselectivity. The cycloadduct obtained was subsequently used as a chiral template to
Total synthesis of jerangolid D
Pospisil, Jiri,Marko, Istvan E.
, p. 3516 - 3517 (2008/01/01)
A short and convergent synthesis of jerangolid D is described. As key steps, a Blaise reaction is employed to construct the lactone ring, a diastereoselective multicomponent Sakurai condensation leads to the dihydropyran ring, and the skipped diene is ass
Formal total synthesis of (+)-methynolide
Cossy, Janine,Bauer, David,Bellosta, Ve?ronique
, p. 715 - 718 (2007/10/03)
A convergent total synthesis of (+)-methynolide was achieved in 23 steps highlighted by a ring-closing metathesis, a Takai reaction, a Sharpless kinetic resolution of an allylic alcohol and a crotylboration.
Formal total synthesis of (+)-methynolide
Cossy, Janine,Bauer, David,Bellosta, Véronique
, p. 5909 - 5922 (2007/10/03)
A formal total synthesis of (+)-methynolide was achieved in 23 steps highlighted by a crotylboration, a ring-closing metathesis, a Sharpless kinetic resolution of an allylic alcohol and a Takai reaction.
An amino alcohol ligand for highly enantioselective addition of organozinc reagents to aldehydes: Serendipity rules
Nugent, William A.
, p. 2133 - 2136 (2007/10/03)
(matrix presented) Amino alcohol 4 (or its enantiomer) is prepared in two simple steps. Commercial (1R,2S)-2-amino-1,2-diphenylethanol is dialkylated with bis(2-bromoethyl) ether. Subsequent hydrogenation over 5% Rh on alumina in the presence of morpholine unexpectedly stops at the hexahydro derivative 4. Amino alcohol 4 promotes the enantioselective addition of diethylzinc to aldehydes at room temperature in up to 99% enantiomeric excess.
Total synthesis of (-)-denticulatins A and B using efficient methods of acyclic stereocontrol
Paterson, Ian,Perkins, Michael V.
, p. 1811 - 1834 (2007/10/03)
The total synthesis of (-)-denticulatin B (2) was achieved in 9 steps (20% yield), with 70% overall diastereoselectivity, starting from the ethyl ketone (R)-9. Most of the stereochemistry was introduced by substrate-based control. Key steps include the boron-mediated aldol/reduction, 9 → 22, the titanium-mediated aldol-coupling. 26 + 8 → 38, and the directed cyclisation, 35 → 2. Epimerisation at C10 in 35 led to (-)-denticulatin A (1).
An Efficiente Preperation of Optically Active Allylic Alcohols, 2-Furyl Alcohols and 2-Thienyl Alcohols by Catalytic Asymmetric Alkylation
Hayashi, Masahiko,Kaneko, Toshiyuki,Oguni, Nobuki
, p. 25 - 28 (2007/10/02)
Highly enantioselective alkylation of some kinds of α,β-unsaturated aldehydes with dialkylzinc proceed in the presence of a small amount of a chiral β-amino alcohol, thus providing an efficient method of obtaining optically active secondary allylic alcohols.Optically active 2-furyl and 2-thienyl alcohols are also available by this catalytic asymmetric alkylation method.
