Pheym Og Chum-1
Asymmeric Synthesis
Parttal and Abaolute Aaymvehric Synthesis Dr. Parjanya Shukla
&
Dr. M. P. Singh Ctassets
When a asyoMMetii Compomel Coithciya lrben) ipb
Synthasi2td by a Byommehic compoomed im movmal Coreliban
the pduct is q aemic mixure
1Auth a Aynthesis iS Ceriad undar csymmetic
inuente Ceithar ophtally acrive rraenh catalyst et), Only
one anamtioaY in dermucl Ceithur 4) o rE)) .
his mum In vohich an asymmtieCwmpoumod s
synthasized y o m m e t m c Compoumal o yielel t)isomuY
aY somer oindly l Lallud Aymmtric ynthsis
3Dr ngmya kr Shukla
ExoAmpl Racluhion af eyruvic atid with HINi ive
acemiC mixtue t ) lache acid
But o h n pyruvic acid rduud by east er im
it ives omly )leche
Lym Leachc atid cuhyehvgenaS
acic
CH CHa
HN H-CoH OH-¢TH ordipy
CH CoOH Synthas
Lach' c qud ) Lachiequd
CODH
youvic aid Racamic MixBure
Syrmmtmal
CoMpoyd CH Omly one 2YomomY
oithout chiral yeast H-COH
Lachcauid Hssumonetme
COOH sumthasis
dohydongorask
(G-lachcqu
Asymetric Aynthasis is dlainal as. ComyeTbion of anachia
Coymmetial) Compormd into q chiral (Asyonmetial) Compoumd
in puch a oay that both erantiomeYs deml in unequo
Mounts?
his tpe oreachions done undar tha
intuanus
of o m chira agent, chiral solvant or catalyopt
pesonu ch rularly polenised light at. Dr. Parjanya Shukla
Dr. M.P. Singh
hese racios darms stureoisomeic (enmtiouanic Clases
c
diastrmomeric) prvelucts în umequal aMounts
Amyomatre symthaois Con be of tuoo types
B
A) arviad asymmetic synthabis Dr.Varganya kr Shukla
Aboolurr aymmtrc ynthasis.
A) Vontial avsyomnmaie Aunthub}a It Con b dogind as
ynthesis of a na chial
Caynter oom an achira Canter by using ophically achive
Laents or Codalysts or solvets etn.
Methods f Pavmad asummehic Aynthaois
D Hrst gwration or
Aubstrate controllad asymnehric upthuis
n this Method ha subtotrate id usually a pume enantiomur
omaturad ogin A nauo chiral Center a t dermd
under the imfuenu a host alhtady presint
Eyarmple hycwboration ot )-isopulagol , new chirol anter
dovm amady prestnt chiral cor quiela th
atac o hyehoboopn doom the reorc moletule
H H
H,THA
H
o'C
H HO
HO
HO H NaOHH
HO H Ne
-CH H
H 3 Cayh
Chira
-isopudagol
TR,2s,s R
H-B
H
OH
(-)elarivative(a)
Irenneeliota) Nw chhral hae
S Cenqusattom
2 Secorel-geneyatiom Methods. Use of chiral auxiliades.
Dr. Parjanya Shukla
hese veactioms conollud by auxilay uwhieh Dr. M.P. Singh Clases
r e chira molatuly ( ovicle. aobli tom Aupprt).
In thuse ynthsis chirality is intrducal by tha attachunant
a a chira quxilary (suppert) uoich dlincs tha
ntiou
Aubegusnt actom Jor the dTmotiom o one
A}tr Cornplating octiem auriloy jirmlly ovecl
Exruplefomotion of lachicacil M pyuvic auid oith
the halp of e mnthol las chiral auxieny)
OH sstianen
HO H
Pynuvic aid --Manthol Munthy pyruvate
(Symnehric) Cauxi ory)
H2/Ni
Nao chiral Aacluehion
OH
on HHo
bH
HO
+ 2Movo
auxilou4 meythy loctate
Elachic aud -Manthe
ryomnetme) 5 r-lonmamya rShukla
3) 3 qcrncrorion Methors Use o chial Vtagents
which
In a chirad pwcuct Jormaal diety by treating
am achiral Atartin compoumal usith a chiral 7ogenk
oith iAlHy in nsone
Exomplk Realuchion) a povpiophenone
ot pooli-cerivec oiamine gives S-l- phanyl povpon-l-ol.
Ho .H
+ HN
LiA CH GHs Dr. Parjanya Shukla
Dr. M. P.
Singh Classes
Poppiophenone Sl-phavng-prpan-
-ol
Achirod)
(SynonehMc)
chiral 30%) Chiral Compownel)
Raogen) (Pymehie)
)uthgenrariom Methools Use d Chiral catalysts!
Extensiom of 3agsoriom) uohare actiom is infmntael
in the PMSnLa o a chia CatalysF
n3yma-Catalyed achem baloneys to this cluss
ExaMpl Convavbim o E) Lache que m pyuvicaud
by
b oubt r lachc aud olahuchrogenas anzy
e n 15 Pag)
B) Absolute Asummnerie Synthasis: Ih is the syrthasis
ot optoally acive
roclucs oDM achirad ulstoate oithout u d of amy
opticoly achve chamicals (no>agimk catalyot olvent et)
In thuid type o Aythesis a physical presena f chiaiy
Like Ciulatry poloiscol light s netasenry.
Exampla Acdolihon o broomin to 2,4,6 timitoshlbora aive
daxtotatuyy moluct by th uscdl oh Cruletny
polavisee light Cfar tha imduetin of chiality)
Neo chira
NO HH
NOCH=CH- CPL
lo, 3 Br
NO
Syonmede Aubstrate ison
No chial Certuy
Dr errjomya Kr Shukla
Hoo.nt HOD
Krismspit ns.of Phamety
fny ara nodla
