A Practical and Scalable Synthesis of (S)- and (R)-1-(Dimethoxyphosphoryl)allyl Methyl Carbonates
Abstract The preparation of ( S )- and ( R )-1-(dimethoxyphosphoryl)allyl methyl carbonates is achieved on multigram scale from commercially available dimethyl phosphite and acrolein in three steps. The key steps involve an asymmetric Pudovik reaction and enzyme-catalyzed kinetic resolution.
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Veröffentlicht in: | Synthesis (Stuttgart) 2015-12, Vol.47 (23), p.3669-3672 |
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container_issue | 23 |
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container_title | Synthesis (Stuttgart) |
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creator | Roy, Sudeshna Sutivisedsak, Nongnuch Hamper, Bruce C. Lyss, Alexander M. Spilling, Christopher D. |
description | Abstract
The preparation of (
S
)- and (
R
)-1-(dimethoxyphosphoryl)allyl methyl carbonates is achieved on multigram scale from commercially available dimethyl phosphite and acrolein in three steps. The key steps involve an asymmetric Pudovik reaction and enzyme-catalyzed kinetic resolution. |
doi_str_mv | 10.1055/s-0035-1560487 |
format | Article |
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The preparation of (
S
)- and (
R
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The preparation of (
S
)- and (
R
)-1-(dimethoxyphosphoryl)allyl methyl carbonates is achieved on multigram scale from commercially available dimethyl phosphite and acrolein in three steps. The key steps involve an asymmetric Pudovik reaction and enzyme-catalyzed kinetic resolution.</description><subject>psp</subject><issn>0039-7881</issn><issn>1437-210X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNp1kEFLAzEQhYMoWKtXzzm2h9RJstlsj6VaFSqKVfAWskmW3ZLulmQF99-b2l49DG-YN28YPoRuKcwoCHEXCQAXhIocskKeoRHNuCSMwtc5GiVrTmRR0Et0FeMWACTj8xHSC_wWtOkboz3WrcWb1OjSO7wZ2r52sYm4q_BkMyV_9uR9SiiZ3Dc719fdz7Cvu5gqDH6qvR88fknzJEsdyq7VvYvX6KLSPrqbk47R5-rhY_lE1q-Pz8vFmhie8Z6YIufacAZS2MJm2lhnGaNclNbSDFhBM2PyvHKO0YpDlVsJjubM8XlpJBV8jGbHuyZ0MQZXqX1odjoMioI6AFJRHQCpE6AUIMdAXzdu59S2-w5t-vC__V_i3mYN</recordid><startdate>20151201</startdate><enddate>20151201</enddate><creator>Roy, Sudeshna</creator><creator>Sutivisedsak, Nongnuch</creator><creator>Hamper, Bruce C.</creator><creator>Lyss, Alexander M.</creator><creator>Spilling, Christopher D.</creator><general>Georg Thieme Verlag</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20151201</creationdate><title>A Practical and Scalable Synthesis of (S)- and (R)-1-(Dimethoxyphosphoryl)allyl Methyl Carbonates</title><author>Roy, Sudeshna ; Sutivisedsak, Nongnuch ; Hamper, Bruce C. ; Lyss, Alexander M. ; Spilling, Christopher D.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c343t-c863ac32075d8d4acded22135bdd1402814cc66fee21f30f6d70e162e39bc7153</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>psp</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Roy, Sudeshna</creatorcontrib><creatorcontrib>Sutivisedsak, Nongnuch</creatorcontrib><creatorcontrib>Hamper, Bruce C.</creatorcontrib><creatorcontrib>Lyss, Alexander M.</creatorcontrib><creatorcontrib>Spilling, Christopher D.</creatorcontrib><collection>CrossRef</collection><jtitle>Synthesis (Stuttgart)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Roy, Sudeshna</au><au>Sutivisedsak, Nongnuch</au><au>Hamper, Bruce C.</au><au>Lyss, Alexander M.</au><au>Spilling, Christopher D.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Practical and Scalable Synthesis of (S)- and (R)-1-(Dimethoxyphosphoryl)allyl Methyl Carbonates</atitle><jtitle>Synthesis (Stuttgart)</jtitle><addtitle>Synthesis</addtitle><date>2015-12-01</date><risdate>2015</risdate><volume>47</volume><issue>23</issue><spage>3669</spage><epage>3672</epage><pages>3669-3672</pages><issn>0039-7881</issn><eissn>1437-210X</eissn><abstract>Abstract
The preparation of (
S
)- and (
R
)-1-(dimethoxyphosphoryl)allyl methyl carbonates is achieved on multigram scale from commercially available dimethyl phosphite and acrolein in three steps. The key steps involve an asymmetric Pudovik reaction and enzyme-catalyzed kinetic resolution.</abstract><cop>Stuttgart · New York</cop><pub>Georg Thieme Verlag</pub><doi>10.1055/s-0035-1560487</doi><tpages>4</tpages></addata></record> |
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ispartof | Synthesis (Stuttgart), 2015-12, Vol.47 (23), p.3669-3672 |
issn | 0039-7881 1437-210X |
language | eng |
recordid | cdi_crossref_primary_10_1055_s_0035_1560487 |
source | Thieme Connect Journals |
subjects | psp |
title | A Practical and Scalable Synthesis of (S)- and (R)-1-(Dimethoxyphosphoryl)allyl Methyl Carbonates |
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