C,P‐Carbon‐Substituted Phosphorus Ylides

Kolodiazhnyi, Oleg I.

doi:10.1002/9783527613908.ch02

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2013

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“…The erosion of enantiopurity was attributed to the ylide (Ph 3 P=CH 2 ) being too basic. It is well known that phosphonium ylides form stable complexes with alkali metals during the dehydrohalogenation of the phosphonium salt [103]. These complexes react with carbonyl compounds differently.…”

Section: Reviewmentioning

confidence: 99%

Garner’s aldehyde as a versatile intermediate in the synthesis of enantiopure natural products

Passiniemi¹,

Koskinen²

2013

Beilstein J. Org. Chem.

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SummarySince its introduction to the synthetic community in 1984, Garner’s aldehyde has gained substantial attention as a chiral intermediate for the synthesis of numerous amino alcohol derivatives. This review presents some of the most successful carbon chain elongation reactions, namely carbonyl alkylations and olefinations. The literature is reviewed with particular attention on understanding how to avoid the deleterious epimerization of the existing stereocenter in Garner’s aldehyde.

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Section: Reviewmentioning

confidence: 99%