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- W2101860009 abstract "Abstract A chemo‐, regio‐, and stereoselectively controlled reaction is highly desirable, yet challenging in organic synthesis. Diversely substituted cis and trans isomers of 2‐alkyl‐3‐pyrrolidinols, 5‐alkyl‐4‐hydroxy‐2‐pyrrolidinones, β‐hydroxy‐γ‐amino acids, and their higher homologues are key structural units found in numerous drugs, drug candidates, and bioactive natural products. Previously, we established a flexible approach to trans ‐5‐alkyl‐4‐benzyloxy‐2‐pyrrolidinones 14 and trans ‐6‐alkyl‐5‐benzyloxy‐2‐piperidinones 15 . Herein, we report a direct, flexible, moisture insensitive, and highly diastereoselective approach to the corresponding cis diastereomers 16 . This stereocontrolled method is based on the MsOH‐mediated (Ms=methane sulfonyl) reductive dehydroxylation of hemiaminal 12 with NaBH(OAc) 3 . cis ‐5‐Alkyl‐4‐benzyloxy‐2‐pyrrolidinones 16 are useful building blocks for the syntheses of natural products such as (+)‐preussin ( 4 ) and streptopyrrolidine ( 5 ) as well as (3 S ,4 S )‐γ‐alkyl‐β‐hydroxy‐γ‐amino acids ( 6 )." @default.
- W2101860009 created "2016-06-24" @default.
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- W2101860009 date "2012-11-06" @default.
- W2101860009 modified "2023-10-18" @default.
- W2101860009 title "Towards Reaction Control:<i>cis</i>-Diastereoselective Reductive Dehydroxylation of 5-Alkyl-4-Benzyloxy-5-Hydroxy-2-Pyrrolidinones" @default.
- W2101860009 cites W1964355934 @default.
- W2101860009 cites W1966412406 @default.
- W2101860009 cites W1976196202 @default.
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- W2101860009 cites W1980343971 @default.
- W2101860009 cites W1982558875 @default.
- W2101860009 cites W1982832174 @default.
- W2101860009 cites W1984196384 @default.
- W2101860009 cites W1984267257 @default.
- W2101860009 cites W1987502126 @default.
- W2101860009 cites W1988823489 @default.
- W2101860009 cites W1989772178 @default.
- W2101860009 cites W1993686329 @default.
- W2101860009 cites W1994516944 @default.
- W2101860009 cites W1995659816 @default.
- W2101860009 cites W1997792770 @default.
- W2101860009 cites W2000582966 @default.
- W2101860009 cites W2001188508 @default.
- W2101860009 cites W2006850016 @default.
- W2101860009 cites W2011016996 @default.
- W2101860009 cites W2018072914 @default.
- W2101860009 cites W2018174874 @default.
- W2101860009 cites W2018610001 @default.
- W2101860009 cites W2020065070 @default.
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- W2101860009 cites W2049643580 @default.
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- W2101860009 doi "https://doi.org/10.1002/ajoc.201200113" @default.
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