Asymmetric Wittig Type Reactions

Abstract

The Wittig reaction and related methods for synthesis of C=C double bonds belong to the standard repertoire of the synthetic chemist. Studies of asymmetric versions of these reactions have been increasing in recent years and applications of such processes to complex molecule synthesis have begun to emerge. In this review, we will emphasise the recent advances in developing methods and synthetic applications of these reactions, but earlier results will be covered as well to place the recent results in context.

Aldehyde olefination with a ruthenium(II) salen catalyst

“…The catalytic alternative to the classic Wittig reaction has proven to be quite promising [2,3], avoiding the need for stepwise generation of phosphorous ylides under basic conditions. Furthermore, the use of transition metal complexes as catalysts also opens the possibility of efficient asymmetric olefination [4,5]. Accordingly, several catalytic aldehyde and ketone olefination systems have been reported based on Mo [6,7], Re [8][9][10][11][12][13][14][15], Ru and Rh [16][17][18][19][20][21][22], Fe [20,[23][24][25][26][27] and Co [28] complexes.…”

Enzymatic synthesis of chiral P-stereogenic phosphonoacetates

“…Chiral Horner-Wadsworth-Emmons (HWE) reagents are extremely useful for asymmetric olefination of prochiral aldehydes or ketones [1][2][3][4]. However, most of these chiral HWE reagents are restricted to the compounds with non-stereogenic phosphorus atom, which are more easily available than P-stereogenic HWE reagents.…”

Nucleoside substituted perhydro-1λ5-[1,3,2]diazaphospholo[1,5-a]pyridine-1-thione analogues: Synthesis and evaluation of antiviral and antimicrobial activities

“…[1][2][3] In particular, phosphorus heterocyclic compounds with five and six membered consisting of heteroatoms like nitrogen and oxygen have been attained significant interest due to their important applications in organic synthesis 3 and large varieties of biological activities such as herbicidal, 4,5 insecticidal 6 and antimicrobial. 7 Further, the phosphorous compounds with P-N functionality like diazaphospholes have been attained great interest due to their significant medicinal, pesticidal, [8][9][10][11] antiviral, bactericidal, antioxidant, 12 and anti-carcinogenic activities.…”