Thieme Chemistry Journal Awardees - Where Are They Now? Aldol Synthesis by anti-Markovnikov Hydration of Propargyloxy Substrates: Feasibility, Stereospecifity, and Reiterative Alkynylation-Hydration

Abstract

A l d o l S y n t h e s i s b y a n t i -M a r k o v n i k o v H y d r a t i o n o f P r o p a r g y l o x y S u b s t r a t e sAbstract: Aldol derivatives have been synthesized by redox-neutral catalytic anti-Markovnikov hydration of propargyloxy substrates. A reiterative sequence of aldehyde alkynylation and alkyne hydration leads to 1,3-polyol derivatives.

Heteroatoms moving protons: Synthetic and mechanistic studies of bifunctional organometallic catalysis

“…In addition to the work described above, since 2005, several notable reports of pyridylphosphine-enhanced catalysis from other labs have appeared, including in situ alkyne hydration catalysts [41], applications of anti -Markovnikov alkyne hydration to selective organic synthesis [72][73][74], and enhanced nitrile hydration [75]. Ongoing studies in the author's lab include additional applications of alkyne hydration and alkene isomerization, development of polymer-supported versions of the catalysts, and extensions of proton transfer capability to other ligand and reaction types.…”

Structures, Mechanisms, and Results in Bifunctional Catalysis and Related Species Involving Proton Transfer

“…In addition to the work described above, since 2005, several notable reports of pyridylphosphine-enhanced catalysis from other labs have appeared, including in situ alkyne hydration catalysts [27], applications of anti-Markovnikov alkyne hydration to selective organic synthesis [28][29][30], and enhanced nitrile hydration [31]. Ongoing studies in the author's lab include additional applications of alkyne hydration and alkene isomerization, development of polymer-supported versions of the catalysts, and extensions of proton transfer capability to other ligand and reaction types.…”

“…In addition to the work described above, since 2005, several notable reports of pyridylphosphine-enhanced catalysis from other labs have appeared, including in situ alkyne hydration catalysts [27], applications of antiMarkovnikov alkyne hydration to selective organic synthesis [28][29][30], and enhanced nitrile hydration [31].…”

Broad‐Spectrum Catalysts for the Ambient Temperature Anti‐Markovnikov Hydration of Alkynes

“…It is also noteworthy that b-amino or b-hydroxy aldehydes could be prepared with this catalyst (2 ac-2 af, 76-96 %). Unsaturated aldehydes, which are major side products formed in reactions employing 6 and 7, [16] were produced in only minor amounts (4 % for 2 ae and 15 % for 2 af).…”