Transformation of cyclic α-phenylthio aldehydes by stereoselective aldol reactions and phenylthio migration into spirocyclic lactones and ethers, and E-allylic alcohols with 1,4-related chiral centres
- 1 January 1991
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 2,p. 451-460
- https://doi.org/10.1039/p19910000451
Abstract
syn- and anti-Selective aldol reactions between enolates of propionate esters and three α-phenylthio cycloalkanecarbaldehydes give single diastereoisomers of phenylthio alcohols which rearrange in acid with 5-hydroxy or 5-CO2H participation to give spirocyclic ethers or lactones. In the absence of internal nucleophiles, allylic sulphides are formed which are used to make allylic alcohols with an E double bond exo to the ring and two stereochemically defined 1,4-related chiral centres.Keywords
This publication has 25 references indexed in Scilit:
- Synthesis of cyclic allylic sulphides (ring sizes 5–15)via phenylthio participationJournal of the Chemical Society, Perkin Transactions 1, 1989
- Synthetic Applications of Double Functionalization by Cooperating Sulfur- and Oxygen-Containing SubstituentsSynthesis, 1988
- A Novel Synthesis of 1-Benzothiophenes from 2-(Phenylthio)-aldehydesSynthesis, 1985
- 1,4-Stereoselection by sequential aldol addition–Claisen rearrangement. Stereostructure of the C30diol from Messel shale kerogenJournal of the Chemical Society, Chemical Communications, 1983
- Synthesis of butenolides from α-(phenylthio)-ketones and -esters: crystal structure of an intermediate β-phenylthio-γ-lactonJournal of the Chemical Society, Perkin Transactions 1, 1981
- Acyclic stereoselection. 4. Assignment of stereostructure to .beta.-hydroxycarbonyl compounds by carbon-13 nuclear magnetic resonanceThe Journal of Organic Chemistry, 1979
- Phenylseleno- and phenylsulfenolactonizations. Two highly efficient and synthetically useful cyclization proceduresJournal of the American Chemical Society, 1979
- Scope and limitations of allyl sulphide synthesis by [1,2] and [1,3] phenylthio migrationJournal of the Chemical Society, Perkin Transactions 1, 1977
- Mechanism of the [1,3] phenylthio shift in the rearrangement of allyl sulphidesJournal of the Chemical Society, Perkin Transactions 1, 1976
- Unsaturated carbenes from primary vinyl triflates. I. Method and scopeJournal of the American Chemical Society, 1974